TWI330183B - - Google Patents

Download PDF

Info

Publication number: TWI330183B
Authority: TW; Taiwan
Prior art keywords: group; substituent; compound; substituted; amino
Prior art date: 2001-10-22

Application number

TW091124227A

Other languages

English (en)

Chinese (zh)

Inventor

Hitoshi Harada

Asano Osamu

Masato Ueda

Shuhei Miyazawa

Kotake Yoshihiko

Daisuke Iida

Junichi Nagakawa

Original Assignee

Eisai R&D Man Co Ltd

Priority date (The priority date 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 date listed.)

2001-10-22

Filing date

2002-10-21

Publication date

2010-09-11

2002-10-21 Application filed by Eisai R&D Man Co Ltd filed Critical Eisai R&D Man Co Ltd

2010-09-11 Application granted granted Critical

2010-09-11 Publication of TWI330183B publication Critical patent/TWI330183B/zh

Links

125000001424 substituent group Chemical group 0.000 claims abstract description 579
150000001875 compounds Chemical class 0.000 claims abstract description 226
150000003839 salts Chemical class 0.000 claims abstract description 95
125000000217 alkyl group Chemical group 0.000 claims abstract description 81
239000012453 solvate Substances 0.000 claims abstract description 66
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 54
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
125000003342 alkenyl group Chemical group 0.000 claims abstract description 37
125000000304 alkynyl group Chemical group 0.000 claims abstract description 36
125000004429 atom Chemical group 0.000 claims abstract description 34
125000005843 halogen group Chemical group 0.000 claims abstract description 28
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 24
229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 22
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 20
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
125000004434 sulfur atom Chemical group 0.000 claims abstract description 18
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 15
230000003042 antagnostic effect Effects 0.000 claims abstract description 6
239000002904 solvent Substances 0.000 claims description 74
238000004519 manufacturing process Methods 0.000 claims description 72
238000000034 method Methods 0.000 claims description 63
125000003118 aryl group Chemical group 0.000 claims description 60
OIRDTQYFTABQOQ-KQYNXXCUSA-N Adenosine Natural products C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 52
102000005962 receptors Human genes 0.000 claims description 46
108020003175 receptors Proteins 0.000 claims description 46
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 42
206010010774 Constipation Diseases 0.000 claims description 41
150000002576 ketones Chemical class 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 38
239000003795 chemical substances by application Substances 0.000 claims description 33
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 28
229960005305 adenosine Drugs 0.000 claims description 28
238000012360 testing method Methods 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 27
239000007789 gas Substances 0.000 claims description 26
125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000003277 amino group Chemical group 0.000 claims description 21
125000004076 pyridyl group Chemical group 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
239000010949 copper Substances 0.000 claims description 14
208000018737 Parkinson disease Diseases 0.000 claims description 13
230000001737 promoting effect Effects 0.000 claims description 12
230000013872 defecation Effects 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000005133 alkynyloxy group Chemical group 0.000 claims description 7
208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
102000007471 Adenosine A2A receptor Human genes 0.000 claims description 6
108010085277 Adenosine A2A receptor Proteins 0.000 claims description 6
102000007470 Adenosine A2B Receptor Human genes 0.000 claims description 6
108010085273 Adenosine A2B receptor Proteins 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000005109 alkynylthio group Chemical group 0.000 claims description 6
208000003243 intestinal obstruction Diseases 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
229930024421 Adenine Natural products 0.000 claims description 5
206010010356 Congenital anomaly Diseases 0.000 claims description 5
229960000643 adenine Drugs 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
210000002216 heart Anatomy 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
230000001079 digestive effect Effects 0.000 claims description 4
230000004064 dysfunction Effects 0.000 claims description 4
210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
125000005577 anthracene group Chemical group 0.000 claims description 3
238000004090 dissolution Methods 0.000 claims description 3
230000002496 gastric effect Effects 0.000 claims description 3
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
239000002689 soil Substances 0.000 claims description 3
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
238000001356 surgical procedure Methods 0.000 claims description 2
238000000338 in vitro Methods 0.000 claims 6
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims 2
BZRIWDPKOVQWII-UHFFFAOYSA-N 1-methyl-1H-acridin-2-one Chemical compound CC1C(C=CC2=NC3=CC=CC=C3C=C12)=O BZRIWDPKOVQWII-UHFFFAOYSA-N 0.000 claims 1
UWDHESVDMJZCAI-UHFFFAOYSA-N 2-pyridin-2-yl-4h-pyridin-3-one Chemical compound O=C1CC=CN=C1C1=CC=CC=N1 UWDHESVDMJZCAI-UHFFFAOYSA-N 0.000 claims 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
QONUMVWLFMVXOC-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methoxyethyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCOC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 QONUMVWLFMVXOC-UHFFFAOYSA-N 0.000 claims 1
JGNIOSOZBWBDNF-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methylbutyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 JGNIOSOZBWBDNF-UHFFFAOYSA-N 0.000 claims 1
HVWYNEQNUCTRPO-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-octylpyridin-2-one Chemical compound C1=CC(=O)N(CCCCCCCC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 HVWYNEQNUCTRPO-UHFFFAOYSA-N 0.000 claims 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
201000009030 Carcinoma Diseases 0.000 claims 1
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims 1
125000002228 disulfide group Chemical group 0.000 claims 1
125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
-1 pyrimidine compound Chemical class 0.000 abstract description 320
125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 133
102000009346 Adenosine receptors Human genes 0.000 abstract description 15
108050000203 Adenosine receptors Proteins 0.000 abstract description 15
101150078577 Adora2b gene Proteins 0.000 abstract description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract description 5
125000002252 acyl group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 196
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 145
238000006243 chemical reaction Methods 0.000 description 135
239000002585 base Substances 0.000 description 122
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
230000015572 biosynthetic process Effects 0.000 description 63
150000004945 aromatic hydrocarbons Chemical group 0.000 description 62
238000003786 synthesis reaction Methods 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
235000019439 ethyl acetate Nutrition 0.000 description 58
239000007858 starting material Substances 0.000 description 58
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 46
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
239000002253 acid Substances 0.000 description 42
239000000243 solution Substances 0.000 description 40
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
150000001412 amines Chemical class 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000007864 aqueous solution Substances 0.000 description 23
229920006395 saturated elastomer Polymers 0.000 description 23
239000003153 chemical reaction reagent Substances 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
101150041968 CDC13 gene Proteins 0.000 description 19
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
229910052783 alkali metal Inorganic materials 0.000 description 19
230000027455 binding Effects 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 18
201000010099 disease Diseases 0.000 description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 17
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
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 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
229940079593 drug Drugs 0.000 description 15
150000002429 hydrazines Chemical class 0.000 description 15
239000001257 hydrogen Substances 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
125000000714 pyrimidinyl group Chemical group 0.000 description 15
239000011734 sodium Substances 0.000 description 15
229910052708 sodium Inorganic materials 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 14
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
239000000725 suspension Substances 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
239000013078 crystal Substances 0.000 description 13
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 13
239000012046 mixed solvent Substances 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
230000001225 therapeutic effect Effects 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
229940044551 receptor antagonist Drugs 0.000 description 11
239000002464 receptor antagonist Substances 0.000 description 11
125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
150000001454 anthracenes Chemical class 0.000 description 10
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
150000003230 pyrimidines Chemical class 0.000 description 10
239000002994 raw material Substances 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
239000010410 layer Substances 0.000 description 9
229920000609 methyl cellulose Polymers 0.000 description 9
235000010981 methylcellulose Nutrition 0.000 description 9
239000001923 methylcellulose Substances 0.000 description 9
239000007800 oxidant agent Substances 0.000 description 9
230000000069 prophylactic effect Effects 0.000 description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 9
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 9
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
241000220317 Rosa Species 0.000 description 8
229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
150000008041 alkali metal carbonates Chemical class 0.000 description 8
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 8
229910052921 ammonium sulfate Inorganic materials 0.000 description 8
235000011130 ammonium sulphate Nutrition 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
229910000042 hydrogen bromide Inorganic materials 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
210000003141 lower extremity Anatomy 0.000 description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
235000019270 ammonium chloride Nutrition 0.000 description 7
239000012267 brine Substances 0.000 description 7
150000001721 carbon Chemical group 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
206010012601 diabetes mellitus Diseases 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
229960005181 morphine Drugs 0.000 description 7
239000000843 powder Substances 0.000 description 7
230000003449 preventive effect Effects 0.000 description 7
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
229940124597 therapeutic agent Drugs 0.000 description 7
229940086542 triethylamine Drugs 0.000 description 7
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
206010036790 Productive cough Diseases 0.000 description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
239000000872 buffer Substances 0.000 description 6
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
239000004914 cyclooctane Substances 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 6
125000002541 furyl group Chemical group 0.000 description 6
125000002883 imidazolyl group Chemical group 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
230000000968 intestinal effect Effects 0.000 description 6
229910052744 lithium Inorganic materials 0.000 description 6
125000002560 nitrile group Chemical group 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
208000024794 sputum Diseases 0.000 description 6
210000003802 sputum Anatomy 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
206010012689 Diabetic retinopathy Diseases 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
208000008589 Obesity Diseases 0.000 description 5
208000001132 Osteoporosis Diseases 0.000 description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
125000003282 alkyl amino group Chemical group 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
230000000172 allergic effect Effects 0.000 description 5
239000003472 antidiabetic agent Substances 0.000 description 5
239000002220 antihypertensive agent Substances 0.000 description 5
208000006673 asthma Diseases 0.000 description 5
208000010668 atopic eczema Diseases 0.000 description 5
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
238000001816 cooling Methods 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000002934 diuretic Substances 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
239000003623 enhancer Substances 0.000 description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000000762 glandular Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
229940126904 hypoglycaemic agent Drugs 0.000 description 5
125000002632 imidazolidinyl group Chemical group 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 5
230000009871 nonspecific binding Effects 0.000 description 5
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
235000020824 obesity Nutrition 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
125000000168 pyrrolyl group Chemical group 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052707 ruthenium Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
235000000346 sugar Nutrition 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
208000011580 syndromic disease Diseases 0.000 description 5
239000003826 tablet Substances 0.000 description 5
229940126585 therapeutic drug Drugs 0.000 description 5
210000001364 upper extremity Anatomy 0.000 description 5
WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 4
102000000506 Adenosine A2 Receptors Human genes 0.000 description 4
108010041368 Adenosine A2 Receptors Proteins 0.000 description 4
101150051188 Adora2a gene Proteins 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
208000011231 Crohn disease Diseases 0.000 description 4
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 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
208000022559 Inflammatory bowel disease Diseases 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 description 4
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
125000003302 alkenyloxy group Chemical group 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
125000006319 alkynyl amino group Chemical group 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
150000004056 anthraquinones Chemical class 0.000 description 4
239000003963 antioxidant agent Substances 0.000 description 4
235000006708 antioxidants Nutrition 0.000 description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
210000004907 gland Anatomy 0.000 description 4
239000003365 glass fiber Substances 0.000 description 4
239000008103 glucose Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000001072 heteroaryl group Chemical group 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000002697 manganese compounds Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
210000004379 membrane Anatomy 0.000 description 4
239000012528 membrane Substances 0.000 description 4
125000002757 morpholinyl group Chemical group 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000003226 pyrazolyl group Chemical group 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 3
PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 3
ZRECPFOSZXDFDT-UHFFFAOYSA-N 1-decylpyrrolidin-2-one Chemical compound CCCCCCCCCCN1CCCC1=O ZRECPFOSZXDFDT-UHFFFAOYSA-N 0.000 description 3
PGNRLPTYNKQQDY-UHFFFAOYSA-N 2,3-dihydroxyindole Chemical group C1=CC=C2C(O)=C(O)NC2=C1 PGNRLPTYNKQQDY-UHFFFAOYSA-N 0.000 description 3
PZNCKJDSGSPNMQ-UHFFFAOYSA-N 2-(2-fluoropyridin-4-yl)-1-(furan-2-yl)ethanone Chemical compound C1=NC(F)=CC(CC(=O)C=2OC=CC=2)=C1 PZNCKJDSGSPNMQ-UHFFFAOYSA-N 0.000 description 3
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
GBAZMCPSNXEWPF-UHFFFAOYSA-N 7,9-dihydro-3h-purine-2,8-dithione Chemical compound C1=NC(=S)NC2=C1NC(=S)N2 GBAZMCPSNXEWPF-UHFFFAOYSA-N 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
208000002249 Diabetes Complications Diseases 0.000 description 3
206010012655 Diabetic complications Diseases 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
206010022489 Insulin Resistance Diseases 0.000 description 3
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229930182558 Sterol Natural products 0.000 description 3
XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
GUQSCTMNEWWGCC-UHFFFAOYSA-L [O-]OOOOOOOO[O-].[Na+].[Na+] Chemical compound [O-]OOOOOOOO[O-].[Na+].[Na+] GUQSCTMNEWWGCC-UHFFFAOYSA-L 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
102000030621 adenylate cyclase Human genes 0.000 description 3
108060000200 adenylate cyclase Proteins 0.000 description 3
125000005108 alkenylthio group Chemical group 0.000 description 3
150000001345 alkine derivatives Chemical class 0.000 description 3
125000005087 alkynylcarbonyl group Chemical group 0.000 description 3
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
229940030600 antihypertensive agent Drugs 0.000 description 3
125000002102 aryl alkyloxo group Chemical group 0.000 description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
235000001465 calcium Nutrition 0.000 description 3
229910001424 calcium ion Inorganic materials 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
230000030833 cell death Effects 0.000 description 3
CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 3
229910000422 cerium(IV) oxide Inorganic materials 0.000 description 3
239000003086 colorant Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
239000012043 crude product Substances 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
230000007850 degeneration Effects 0.000 description 3
FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 3
238000009826 distribution Methods 0.000 description 3
230000001882 diuretic effect Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
210000003608 fece Anatomy 0.000 description 3
239000000835 fiber Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
210000003194 forelimb Anatomy 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 3
125000000842 isoxazolyl group Chemical group 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
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 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
239000003002 pH adjusting agent Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
125000005561 phenanthryl group Chemical group 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
125000000719 pyrrolidinyl group Chemical group 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
235000003702 sterols Nutrition 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
125000003831 tetrazolyl group Chemical group 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
229930192474 thiophene Natural products 0.000 description 3
125000001425 triazolyl group Chemical group 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
210000003462 vein Anatomy 0.000 description 3
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
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 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 2
CQVWOJSAGPFDQL-UHFFFAOYSA-N 3-iodopropan-1-ol Chemical compound OCCCI CQVWOJSAGPFDQL-UHFFFAOYSA-N 0.000 description 2
JTOGGBLTIHXWEH-UHFFFAOYSA-N 4-(furan-2-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2OC=CC=2)=N1 JTOGGBLTIHXWEH-UHFFFAOYSA-N 0.000 description 2
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
QEFGSYOHUBGGJW-UHFFFAOYSA-N 5-bromo-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound BrC=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 QEFGSYOHUBGGJW-UHFFFAOYSA-N 0.000 description 2
150000005697 5-halopyrimidines Chemical class 0.000 description 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
229940127600 A2A receptor antagonist Drugs 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
239000004375 Dextrin Substances 0.000 description 2
229920001353 Dextrin Polymers 0.000 description 2
208000012661 Dyskinesia Diseases 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
229940124382 agent for constipation Drugs 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
125000005336 allyloxy group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000010775 animal oil Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000003934 aromatic aldehydes Chemical class 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000004069 aziridinyl group Chemical group 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
235000013405 beer Nutrition 0.000 description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
210000005252 bulbus oculi Anatomy 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229910000420 cerium oxide Inorganic materials 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
230000000112 colonic effect Effects 0.000 description 2
239000002299 complementary DNA Substances 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
229930003836 cresol Natural products 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000002950 deficient Effects 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229930004069 diterpene Natural products 0.000 description 2
150000004141 diterpene derivatives Chemical class 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
239000003651 drinking water Substances 0.000 description 2
235000020188 drinking water Nutrition 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
210000003414 extremity Anatomy 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000002309 gasification Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
229940014259 gelatin Drugs 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
125000006038 hexenyl group Chemical group 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
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
125000001786 isothiazolyl group Chemical group 0.000 description 2
229960003299 ketamine Drugs 0.000 description 2
239000003446 ligand Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
230000007774 longterm Effects 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
150000004706 metal oxides Chemical class 0.000 description 2
230000007659 motor function Effects 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
DSWNRHCOGVRDOE-UHFFFAOYSA-N n,n-dimethylmethanimidamide Chemical compound CN(C)C=N DSWNRHCOGVRDOE-UHFFFAOYSA-N 0.000 description 2
125000006606 n-butoxy group Chemical group 0.000 description 2
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
210000005036 nerve Anatomy 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
239000012038 nucleophile Substances 0.000 description 2
230000000414 obstructive effect Effects 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000002971 oxazolyl group Chemical group 0.000 description 2
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000001814 pectin Substances 0.000 description 2
235000010987 pectin Nutrition 0.000 description 2
229920001277 pectin Polymers 0.000 description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
210000003200 peritoneal cavity Anatomy 0.000 description 2
125000005936 piperidyl group Chemical group 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
229950008882 polysorbate Drugs 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000011533 pre-incubation Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 2
125000003072 pyrazolidinyl group Chemical group 0.000 description 2
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
125000001422 pyrrolinyl group Chemical group 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
125000005493 quinolyl group Chemical group 0.000 description 2
150000004060 quinone imines Chemical class 0.000 description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
230000004044 response Effects 0.000 description 2
VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical group [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 2
239000000523 sample Substances 0.000 description 2
238000012163 sequencing technique Methods 0.000 description 2
HUJXHFRXWWGYQH-UHFFFAOYSA-O sinapine Chemical compound COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O HUJXHFRXWWGYQH-UHFFFAOYSA-O 0.000 description 2
239000000779 smoke Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
150000003432 sterols Chemical class 0.000 description 2
210000003523 substantia nigra Anatomy 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
210000003932 urinary bladder Anatomy 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
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
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
125000004733 1,1,2-trimethylpropylthio group Chemical group CC(C(C)C)(S*)C 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
SJQBHNHASPQACB-UHFFFAOYSA-N 1,2-dimethoxyethene Chemical compound COC=COC SJQBHNHASPQACB-UHFFFAOYSA-N 0.000 description 1
UPNNXUSUOSTIIM-UHFFFAOYSA-N 1,2-dithietane Chemical compound C1CSS1 UPNNXUSUOSTIIM-UHFFFAOYSA-N 0.000 description 1
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
MJVIGUCNSRXAFO-UHFFFAOYSA-N 1,3-dipropyl-7h-purine-2,6-dione Chemical compound O=C1N(CCC)C(=O)N(CCC)C2=C1NC=N2 MJVIGUCNSRXAFO-UHFFFAOYSA-N 0.000 description 1
KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
GIHLXJXOKBHWJA-UHFFFAOYSA-N 1,8-dipropyl-3,7-dihydropurine-2,6-dione Chemical compound N1C(=O)N(CCC)C(=O)C2=C1N=C(CCC)N2 GIHLXJXOKBHWJA-UHFFFAOYSA-N 0.000 description 1
QBAVHEZVBGASER-UHFFFAOYSA-N 1-(2-bromoethyl)pyrrole Chemical compound BrCCN1C=CC=C1 QBAVHEZVBGASER-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-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
VNHWPVLQRKKKRY-UHFFFAOYSA-N 1-bromo-3-fluoropropane Chemical compound FCCCBr VNHWPVLQRKKKRY-UHFFFAOYSA-N 0.000 description 1
LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 1
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
MTVUDFBYBPMGMR-UHFFFAOYSA-N 1-ethyl-2-propylhydrazine Chemical compound CCCNNCC MTVUDFBYBPMGMR-UHFFFAOYSA-N 0.000 description 1
LVYJIIRJQDEGBR-UHFFFAOYSA-N 1-fluoro-2-iodoethane Chemical compound FCCI LVYJIIRJQDEGBR-UHFFFAOYSA-N 0.000 description 1
MTLSGNSSRQHXQO-UHFFFAOYSA-N 1-methoxyacridine Chemical compound C1=CC=C2C=C3C(OC)=CC=CC3=NC2=C1 MTLSGNSSRQHXQO-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000006023 1-pentenyl group Chemical group 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical group C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 description 1
ZMJBHCIEMIVIFZ-UHFFFAOYSA-N 2,3-dimethylthiirane Chemical compound CC1SC1C ZMJBHCIEMIVIFZ-UHFFFAOYSA-N 0.000 description 1
ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical compound CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 1
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
LDISDPBIDUIBOC-UHFFFAOYSA-N 2-bromoethylhydrazine Chemical compound NNCCBr LDISDPBIDUIBOC-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical compound C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
CGCOPLAFHQVQEL-UHFFFAOYSA-N 2-ethylsulfanylfuran Chemical group CCSC1=CC=CO1 CGCOPLAFHQVQEL-UHFFFAOYSA-N 0.000 description 1
YBQXKYLRISIJBE-UHFFFAOYSA-N 2-fluoro-1h-pyridine-4-thione Chemical compound FC1=CC(=S)C=CN1 YBQXKYLRISIJBE-UHFFFAOYSA-N 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical group [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 description 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
UFVNXLNHTPDYGT-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-[2-(propan-2-ylamino)pyridin-4-yl]pyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 UFVNXLNHTPDYGT-UHFFFAOYSA-N 0.000 description 1
YTUDVELGWQFAPK-UHFFFAOYSA-N 4,6-bis(furan-2-yl)-5-[2-(propylamino)pyridin-4-yl]pyrimidin-2-amine Chemical compound C1=NC(NCCC)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 YTUDVELGWQFAPK-UHFFFAOYSA-N 0.000 description 1
JBAJMLMKIIDEJX-UHFFFAOYSA-N 4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound N=1C(N)=NC(C=2OC=CC=2)=CC=1C1=CC=CO1 JBAJMLMKIIDEJX-UHFFFAOYSA-N 0.000 description 1
QWEUTQRWNFQNKG-UHFFFAOYSA-N 4-(3-fluorophenyl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=C(F)C=CC=2)=N1 QWEUTQRWNFQNKG-UHFFFAOYSA-N 0.000 description 1
JZMZHCKCWHVWBE-UHFFFAOYSA-N 4-(furan-2-yl)-6-methyl-5-pyridin-4-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C=NC=CC=1C=1C(C)=NC(N)=NC=1C1=CC=CO1 JZMZHCKCWHVWBE-UHFFFAOYSA-N 0.000 description 1
IUTHGAAXFHBXRJ-UHFFFAOYSA-N 4-chloro-6-(furan-2-yl)-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC(Cl)=C1C1=CC=NC=C1 IUTHGAAXFHBXRJ-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
FLDSMVTWEZKONL-AWEZNQCLSA-N 5,5-dimethyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound CC1(CC2=C(NN=C2C(=O)N[C@@H]2C(N(C3=C(OC2)C=CC=C3)C)=O)CCO1)C FLDSMVTWEZKONL-AWEZNQCLSA-N 0.000 description 1
DINLWOJVLUFASI-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-phenylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2C=CC=CC=2)=NC(N)=NC=1C1=CC=CO1 DINLWOJVLUFASI-UHFFFAOYSA-N 0.000 description 1
ATFBOSCBLMVFRM-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)-6-pyridin-4-ylpyrimidin-2-amine Chemical compound C=1C=NC(F)=CC=1C=1C(C=2C=CN=CC=2)=NC(N)=NC=1C1=CC=CO1 ATFBOSCBLMVFRM-UHFFFAOYSA-N 0.000 description 1
XFMRAFPIRFRBFU-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(furan-2-yl)pyrimidin-2-amine Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C1=CC=NC(F)=C1 XFMRAFPIRFRBFU-UHFFFAOYSA-N 0.000 description 1
GKHLIODVGUNPLL-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-4-phenylpyrimidin-2-amine Chemical compound C=1C=CC=CC=1C1=NC(N)=NC=C1C1=CC=C(Cl)N=C1 GKHLIODVGUNPLL-UHFFFAOYSA-N 0.000 description 1
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
GVFIYDLZMSJDQZ-UHFFFAOYSA-N 5-[2-(ethylamino)pyridin-4-yl]-4,6-bis(furan-2-yl)pyrimidin-2-amine Chemical compound C1=NC(NCC)=CC(C=2C(=NC(N)=NC=2C=2OC=CC=2)C=2OC=CC=2)=C1 GVFIYDLZMSJDQZ-UHFFFAOYSA-N 0.000 description 1
ZUGAOYSWHHGDJY-UHFFFAOYSA-K 5-hydroxy-2,8,9-trioxa-1-aluminabicyclo[3.3.2]decane-3,7,10-trione Chemical compound [Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZUGAOYSWHHGDJY-UHFFFAOYSA-K 0.000 description 1
KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
GMMWNTHAIOJBSD-UHFFFAOYSA-N 6-chloro-4-n-(2,3-dimethylphenyl)-2-n,2-n-dimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=NC(Cl)=CC(NC=2C(=C(C)C=CC=2)C)=N1 GMMWNTHAIOJBSD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-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
GMXIEASXPUEOTG-UHFFFAOYSA-N 8-bromooctan-1-ol Chemical compound OCCCCCCCCBr GMXIEASXPUEOTG-UHFFFAOYSA-N 0.000 description 1
PJFMAVHETLRJHJ-UHFFFAOYSA-N 8-phenyltheophylline Chemical compound N1C=2C(=O)N(C)C(=O)N(C)C=2N=C1C1=CC=CC=C1 PJFMAVHETLRJHJ-UHFFFAOYSA-N 0.000 description 1
GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
229940124049 Adenosine A2 receptor antagonist Drugs 0.000 description 1
229940123053 Adenosine A2b receptor antagonist Drugs 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000272525 Anas platyrhynchos Species 0.000 description 1
241001061264 Astragalus Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
LIOOYTONWYVYLU-UHFFFAOYSA-N BrCCOCCOCCCCCCCCCC Chemical compound BrCCOCCOCCCCCCCCCC LIOOYTONWYVYLU-UHFFFAOYSA-N 0.000 description 1
RALZZIHXLIBULT-UHFFFAOYSA-N C(C)N(CC)NN.NN Chemical compound C(C)N(CC)NN.NN RALZZIHXLIBULT-UHFFFAOYSA-N 0.000 description 1
ZPPDTQRHSUNLJX-UHFFFAOYSA-N C(CCC)C([O-])CCC.[K+] Chemical compound C(CCC)C([O-])CCC.[K+] ZPPDTQRHSUNLJX-UHFFFAOYSA-N 0.000 description 1
YUDKTOOBWZMDNR-UHFFFAOYSA-N C(CCCCCCCCCCCC)C(CCCCCCCCC)C#N Chemical compound C(CCCCCCCCCCCC)C(CCCCCCCCC)C#N YUDKTOOBWZMDNR-UHFFFAOYSA-N 0.000 description 1
ZTCAXVVNVGISAW-UHFFFAOYSA-N C1(CC1)CCCCCCCCCCBr Chemical compound C1(CC1)CCCCCCCCCCBr ZTCAXVVNVGISAW-UHFFFAOYSA-N 0.000 description 1
PAOANWZGLPPROA-RQXXJAGISA-N CGS-21680 Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(O)=O)=CC=3)=NC(N)=C2N=C1 PAOANWZGLPPROA-RQXXJAGISA-N 0.000 description 1
IUSPSRZKIUBHKS-UHFFFAOYSA-N CN(C)C=CCC1=CC=CO1 Chemical compound CN(C)C=CCC1=CC=CO1 IUSPSRZKIUBHKS-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
108091006146 Channels Proteins 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
241001573498 Compacta Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
101150049660 DRD2 gene Proteins 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
NHXSTXWKZVAVOQ-UHFFFAOYSA-N Ethyl furoate Chemical compound CCOC(=O)C1=CC=CO1 NHXSTXWKZVAVOQ-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
108091006027 G proteins Proteins 0.000 description 1
102000030782 GTP binding Human genes 0.000 description 1
108091000058 GTP-Binding Proteins 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
101000783756 Homo sapiens Adenosine receptor A2b Proteins 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
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 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
206010049816 Muscle tightness Diseases 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
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 description 1
206010028980 Neoplasm Diseases 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
102000004257 Potassium Channel Human genes 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
WCJPFSMEPSYRKA-UHFFFAOYSA-N SOC(N(C)C)OS Chemical compound SOC(N(C)C)OS WCJPFSMEPSYRKA-UHFFFAOYSA-N 0.000 description 1
241000207929 Scutellaria Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000000692 Student's t-test Methods 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
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
244000078534 Vaccinium myrtillus Species 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
235000010724 Wisteria floribunda Nutrition 0.000 description 1
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 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
OFFGGRYUHCEFJC-UHFFFAOYSA-I [Mg+2].[Br-].[Ce+3].[Br-].[Br-].[Br-].[Br-] Chemical compound [Mg+2].[Br-].[Ce+3].[Br-].[Br-].[Br-].[Br-] OFFGGRYUHCEFJC-UHFFFAOYSA-I 0.000 description 1
230000007488 abnormal function Effects 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960005164 acesulfame Drugs 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000003449 adenosine A2 receptor antagonist Substances 0.000 description 1
229940121359 adenosine receptor antagonist Drugs 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000004419 alkynylene group Chemical group 0.000 description 1
125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
230000007815 allergy Effects 0.000 description 1
229940087168 alpha tocopherol Drugs 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
LEWCAQWVBYTPMP-UHFFFAOYSA-K aluminum;magnesium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Mg+2].[Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O LEWCAQWVBYTPMP-UHFFFAOYSA-K 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012805 animal sample Substances 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003579 anti-obesity Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000001509 aspartic acid derivatives Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
235000006533 astragalus Nutrition 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
TXKAQZRUJUNDHI-UHFFFAOYSA-K bismuth tribromide Chemical compound Br[Bi](Br)Br TXKAQZRUJUNDHI-UHFFFAOYSA-K 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229940116229 borneol Drugs 0.000 description 1
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
SZOLUXDHHKCYKT-UHFFFAOYSA-N but-1-en-1-amine Chemical compound CCC=CN SZOLUXDHHKCYKT-UHFFFAOYSA-N 0.000 description 1
ZUCWUADHUDQXHX-UHFFFAOYSA-N but-1-en-2-amine Chemical compound CCC(N)=C ZUCWUADHUDQXHX-UHFFFAOYSA-N 0.000 description 1
OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
239000001354 calcium citrate Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
230000000739 chaotic effect Effects 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
229940077239 chlorous acid Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000002734 clay mineral Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
210000001653 corpus striatum Anatomy 0.000 description 1
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
125000000323 cyclohepten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
125000006612 decyloxy group Chemical group 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
239000002781 deodorant agent Substances 0.000 description 1
230000030609 dephosphorylation Effects 0.000 description 1
238000006209 dephosphorylation reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
241001233061 earthworms Species 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000010696 ester oil Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
QVLJLWHOILVHJJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylacetate Chemical compound CCOC(=O)CC1=CC=NC=C1 QVLJLWHOILVHJJ-UHFFFAOYSA-N 0.000 description 1
XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000003885 eye ointment Substances 0.000 description 1
210000000887 face Anatomy 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000004503 fine granule Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
230000006870 function Effects 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
210000003736 gastrointestinal content Anatomy 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
AKOJBFZCIRFXBA-UHFFFAOYSA-N hexa-1,3-diyne Chemical compound CCC#CC#C AKOJBFZCIRFXBA-UHFFFAOYSA-N 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
102000055126 human ADORA2B Human genes 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
150000002466 imines Chemical group 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
238000009830 intercalation Methods 0.000 description 1
230000002687 intercalation Effects 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
125000005921 isopentoxy group Chemical group 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
239000003410 keratolytic agent Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
238000006138 lithiation reaction Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
125000001288 lysyl group Chemical group 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
DKXULEFCEORBJK-UHFFFAOYSA-N magnesium;octadecanoic acid Chemical compound [Mg].CCCCCCCCCCCCCCCCCC(O)=O DKXULEFCEORBJK-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940086559 methyl benzoin Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000008267 milk Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
YFKNCTBAPAZLON-UHFFFAOYSA-N n,n-dimethyl-1h-indol-2-amine Chemical compound C1=CC=C2NC(N(C)C)=CC2=C1 YFKNCTBAPAZLON-UHFFFAOYSA-N 0.000 description 1
GAFDBAYKQMRIMD-UHFFFAOYSA-N n-(hydroxyamino)hydroxylamine Chemical group ONNO GAFDBAYKQMRIMD-UHFFFAOYSA-N 0.000 description 1
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
SQMWSBKSHWARHU-SDBHATRESA-N n6-cyclopentyladenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(NC3CCCC3)=C2N=C1 SQMWSBKSHWARHU-SDBHATRESA-N 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
239000010955 niobium Substances 0.000 description 1
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
210000001009 nucleus accumben Anatomy 0.000 description 1
229940073665 octyldodecyl myristate Drugs 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000001010 olfactory tubercle Anatomy 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
125000005968 oxazolinyl group Chemical group 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
229960002702 piroxicam Drugs 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
150000004032 porphyrins Chemical group 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
FNVIJAXBJSXSAU-UHFFFAOYSA-N propane;hydrobromide Chemical compound Br.CCC FNVIJAXBJSXSAU-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
210000003370 receptor cell Anatomy 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000035807 sensation Effects 0.000 description 1
235000019615 sensations Nutrition 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000009958 sewing Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000005245 sintering Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
229940032094 squalane Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
125000004354 sulfur functional group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000012353 t test Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003760 tallow Substances 0.000 description 1
210000004233 talus Anatomy 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
235000013337 tricalcium citrate Nutrition 0.000 description 1
125000006168 tricyclic group Chemical group 0.000 description 1
AYVFJPRMOZTEOZ-UHFFFAOYSA-N trihexyltin Chemical compound CCCCCC[Sn](CCCCCC)CCCCCC AYVFJPRMOZTEOZ-UHFFFAOYSA-N 0.000 description 1
LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229940075420 xanthine Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Obesity (AREA)
Physical Education & Sports Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Epidemiology (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Psychology (AREA)
Ophthalmology & Optometry (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW091124227A 2001-10-22 2002-10-21 TWI330183B (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2001324018		2001-10-22

Publications (1)

Publication Number	Publication Date
TWI330183B true TWI330183B (2)	2010-09-11

Family

ID=19140824

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW091124227A TWI330183B (2)	2001-10-22	2002-10-21

Country Status (24)

Country	Link
US (2)	US7396836B2 (2)
EP (2)	EP1439175B1 (2)
JP (1)	JP4462930B2 (2)
KR (1)	KR100884025B1 (2)
CN (1)	CN100519549C (2)
AT (1)	ATE507217T1 (2)
AU (1)	AU2002335536B2 (2)
BR (1)	BR0213455A (2)
CA (1)	CA2463284C (2)
CY (1)	CY1112341T1 (2)
DE (1)	DE60239884D1 (2)
DK (1)	DK1439175T3 (2)
ES (1)	ES2364328T3 (2)
HU (1)	HUP0401950A3 (2)
IL (2)	IL161493A0 (2)
MX (1)	MXPA04003795A (2)
NO (1)	NO327581B1 (2)
NZ (1)	NZ532373A (2)
PL (1)	PL215572B1 (2)
PT (1)	PT1439175E (2)
RU (1)	RU2288227C2 (2)
TW (1)	TWI330183B (2)
WO (1)	WO2003035639A1 (2)
ZA (1)	ZA200402898B (2)

Families Citing this family (115)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI330183B (2) *	2001-10-22	2010-09-11	Eisai R&D Man Co Ltd
AU2002950853A0 (en) *	2002-08-19	2002-09-12	Fujisawa Pharmaceutical Co., Ltd.	Aminopyrimidine compound and pharmaceutical use thereof
ES2229928B1 (es) *	2003-10-02	2006-07-01	Almirall Prodesfarma, S.A.	Nuevos derivados de pirimidin-2-amina.
GB0323138D0 (en) *	2003-10-03	2003-11-05	Chang Lisa C W	Pyrimidines substituted in the 2,4,6 positions and their different uses
GB0323137D0 (en)	2003-10-03	2003-11-05	Chang Lisa C W	2,4,6- Trisubstituted pyrimidines and their different uses
EP1679309A4 (en) *	2003-10-24	2007-03-28	Ono Pharmaceutical Co	ANTISTRESS MEDICAMENT AND ITS MEDICAL USE
RU2006118325A (ru) *	2003-10-27	2007-12-10	Астеллас Фарма Инк. (Jp)	Производные пиразина и их фармацевтическое применение
MXPA06006776A (es) *	2003-12-15	2007-03-23	Almirall Prodesfarma Ag	2,6-bisheteroaril-4-aminopirimidinas como antagonistas del receptor de adenosina.
PL3002283T3 (pl)	2003-12-26	2017-10-31	Kyowa Hakko Kirin Co Ltd	Pochodne tiazolu
US20080125403A1 (en)	2004-04-02	2008-05-29	Merck & Co., Inc.	Method of Treating Men with Metabolic and Anthropometric Disorders
CA2562244A1 (en) *	2004-04-07	2005-10-27	Takeda Pharmaceutical Company Limited	Cyclic compounds
GB2416125A (en) *	2004-07-15	2006-01-18	Michael James Hill	Device for supplying fluid to an ear
US9512125B2 (en)	2004-11-19	2016-12-06	The Regents Of The University Of California	Substituted pyrazolo[3.4-D] pyrimidines as anti-inflammatory agents
GB0428514D0 (en) *	2004-12-31	2005-02-09	Prosidion Ltd	Compounds
WO2006101082A1 (ja) *	2005-03-21	2006-09-28	Eisai R & D Management Co., Ltd.	ピリミジン化合物の結晶、非晶質および製造方法
US7396928B2 (en)	2005-03-21	2008-07-08	Eisai R&D Management Co., Ltd.	Crystals of 5-[2-amino-4-(2-furyl) pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and processes for preparing the same
US7538117B2 (en)	2005-03-21	2009-05-26	Eisai R&D Management Co., Ltd.	Crystalline and amorphous pyrimidine compounds and processes for preparing pyrimidine compounds
US20080275064A1 (en) *	2005-04-11	2008-11-06	Deborah Slee	Substituted Pyrimidines as Adenosine Receptor Antagonists
JP2008544743A (ja)	2005-05-10	2008-12-11	インターミューンインコーポレイテッド	ストレス活性化蛋白質キナーゼ系をモジュレートするためのピリドン誘導体
WO2006137527A1 (ja)	2005-06-23	2006-12-28	Kyowa Hakko Kogyo Co., Ltd.	チアゾール誘導体
ES2270715B1 (es) *	2005-07-29	2008-04-01	Laboratorios Almirall S.A.	Nuevos derivados de pirazina.
PT1921077T (pt)	2005-08-02	2017-10-26	Kyowa Hakko Kirin Co Ltd	Agente para tratar e/ou prevenir distúrbio do sono
ES2274712B1 (es)	2005-10-06	2008-03-01	Laboratorios Almirall S.A.	Nuevos derivados imidazopiridina.
MX2008010953A (es) *	2006-02-28	2008-09-08	Amgen Inc	Derivados de cinolina y quinoxalina como inhibidores de la fosfodiesterasa 10.
TWI417095B (zh)	2006-03-15	2013-12-01	Janssen Pharmaceuticals Inc	１，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途
JP2009532507A (ja)	2006-04-04	2009-09-10	ザリージェンツオブザユニバーシティオブカリフォルニア	Ｐｉ３キナーゼアンタゴニスト
US20080009623A1 (en) *	2006-07-06	2008-01-10	Eisai R&D Management Co., Ltd.	Pyrimidine compounds
JP2009286694A (ja) *	2006-09-07	2009-12-10	Eisai R & D Management Co Ltd	５−［２−アミノ−４−（２−フリル）ピリミジン−５−イル］−１−メチルピリジン−２（１ｈ）−オンの塩およびそれらの結晶
ES2303776B1 (es) *	2006-12-29	2009-08-07	Laboratorios Almirall S.A.	Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b.
TW200845978A (en)	2007-03-07	2008-12-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
TW200900065A (en)	2007-03-07	2009-01-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
CA2694275A1 (en) *	2007-07-26	2009-01-29	Novartis Ag	Organic compounds
PL2203439T3 (pl)	2007-09-14	2011-06-30	Addex Pharmaceuticals Sa	1',3'-dipodstawione-4-fenylo-3,4,5,6-tetrahydro-2H, 1'H-[1, 4']bipirydynylo-2'-ketony
WO2009046448A1 (en) *	2007-10-04	2009-04-09	Intellikine, Inc.	Chemical entities and therapeutic uses thereof
US8193182B2 (en)	2008-01-04	2012-06-05	Intellikine, Inc.	Substituted isoquinolin-1(2H)-ones, and methods of use thereof
MX2010007418A (es)	2008-01-04	2010-11-12	Intellikine Inc	Ciertas entidades quimicas, composiciones y metodos.
WO2009114870A2 (en)	2008-03-14	2009-09-17	Intellikine, Inc.	Kinase inhibitors and methods of use
WO2009114874A2 (en)	2008-03-14	2009-09-17	Intellikine, Inc.	Benzothiazole kinase inhibitors and methods of use
CA2718983C (en)	2008-03-26	2015-12-08	Advinus Therapeutics Pvt. Ltd.	Heterocyclic compounds as adenosine receptor antagonist
MX2010012848A (es)	2008-06-03	2011-03-01	Intermune Inc	Compuestos y metodos para tratar trastornos inflamatorios y fibroticos.
CN101343253B (zh) *	2008-06-24	2011-03-16	陕西师范大学	2-氨基-4,5-二芳基嘧啶类化合物及其制备方法和药物用途
EP3009436B1 (en)	2008-07-08	2019-06-05	Intellikine, LLC	Kinase inhibitors and methods of use
WO2010006072A2 (en)	2008-07-08	2010-01-14	The Regents Of The University Of California	Mtor modulators and uses thereof
ES2439291T3 (es)	2008-09-02	2014-01-22	Janssen Pharmaceuticals, Inc.	Derivados de 3-azabiciclo[3.1.0]hexilo como moduladores de receptores de glutamato metabotrópicos
WO2010036380A1 (en)	2008-09-26	2010-04-01	Intellikine, Inc.	Heterocyclic kinase inhibitors
AU2009305669A1 (en)	2008-10-16	2010-04-22	The Regents Of The University Of California	Fused ring heteroaryl kinase inhibitors
US8476431B2 (en)	2008-11-03	2013-07-02	Itellikine LLC	Benzoxazole kinase inhibitors and methods of use
ES2401691T3 (es)	2008-11-28	2013-04-23	Ortho-Mcneil-Janssen Pharmaceuticals, Inc.	Derivados de indol y de benzoxacina como moduladores de los receptores metabotrópicos de glutamato
AU2010222289B2 (en)	2009-03-13	2013-07-11	Advinus Therapeutics Private Limited	Substituted fused pyrimidine compounds
JP5789252B2 (ja)	2009-05-07	2015-10-07	インテリカイン，エルエルシー	複素環式化合物およびその使用
AU2010246607B2 (en)	2009-05-12	2012-09-27	Addex Pharma S.A.	1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
JP5634506B2 (ja)	2009-05-12	2014-12-03	ジャンセンファーマシューティカルズ，インコーポレイテッド	１，２，３−トリアゾロ［４，３−ａ］ピリジン誘導体ならびに神経障害および精神障害の治療または予防のためのその使用
US8980899B2 (en)	2009-10-16	2015-03-17	The Regents Of The University Of California	Methods of inhibiting Ire1
US8796290B2 (en)	2009-11-09	2014-08-05	Advinus Therapeutics Limited	Substituted fused pyrimidine compounds, its preparation and uses thereof
EP2542077A4 (en) *	2010-03-04	2013-08-21	Merck Sharp & Dohme	HEMMER OF CATECHOL-O-METHYL-TRANSFERASE AND ITS USE IN THE TREATMENT OF PSYCHOTIC DISORDER
ES2365960B1 (es) *	2010-03-31	2012-06-04	Palobiofarma, S.L	Nuevos antagonistas de los receptores de adenosina.
AU2011255218B2 (en)	2010-05-21	2015-03-12	Infinity Pharmaceuticals, Inc.	Chemical compounds, compositions and methods for kinase modulation
WO2012027331A1 (en)	2010-08-27	2012-03-01	Ironwood Pharmaceuticals, Inc.	Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders
CA2810625C (en)	2010-09-13	2018-01-23	Advinus Therapeutics Private Limited	Purine compounds as prodrugs of a2b adenosine receptor antagonists, their process and medicinal applications
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
WO2012039718A1 (en)	2010-09-24	2012-03-29	N30 Pharmaceuticals, Llc	Novel dihydropyrimidin-2(1h)-one compounds as neurokinin-3 receptor antagonists
JP5852665B2 (ja)	2010-11-08	2016-02-03	ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド	１，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体のポジティブアロステリックモジュレーターとしてのそれらの使用
JP5852666B2 (ja)	2010-11-08	2016-02-03	ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド	１，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体のポジティブアロステリックモジュレーターとしてのそれらの使用
ES2552455T3 (es)	2010-11-08	2015-11-30	Janssen Pharmaceuticals, Inc.	Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2
JP2013545749A (ja)	2010-11-10	2013-12-26	インフィニティーファーマシューティカルズ，インコーポレイテッド	複素環化合物及びその使用
US8809349B2 (en)	2011-01-10	2014-08-19	Infinity Pharmaceuticals, Inc.	Processes for preparing isoquinolinones and solid forms of isoquinolinones
CA2828483A1 (en)	2011-02-23	2012-11-01	Intellikine, Llc	Combination of kinase inhibitors and uses thereof
CZ305457B6 (cs) *	2011-02-28	2015-09-30	Ústav organické chemie a biochemie, Akademie věd ČR v. v. i.	Pyrimidinové sloučeniny inhibující tvorbu oxidu dusnatého a prostaglandinu E2, způsob výroby a použití
EP2734520B1 (en)	2011-07-19	2016-09-14	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
EP2734530A1 (en)	2011-07-19	2014-05-28	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
JP6029668B2 (ja)	2011-08-29	2016-11-24	インフィニティーファーマシューティカルズ，インコーポレイテッド	複素環式化合物及びその使用
JP6342805B2 (ja)	2011-09-02	2018-06-13	ザリージェンツオブザユニバーシティオブカリフォルニア	置換ピラゾロ［３，４−ｄ］ピリミジンおよびその用途
PT2820009T (pt) *	2012-03-01	2018-04-12	Array Biopharma Inc	Inibidores de serina/treonina quinases
US8940742B2 (en)	2012-04-10	2015-01-27	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
US8828998B2 (en)	2012-06-25	2014-09-09	Infinity Pharmaceuticals, Inc.	Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
SG11201502331RA (en)	2012-09-26	2015-04-29	Univ California	Modulation of ire1
AR092742A1 (es)	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
SMT201800561T1 (it)	2012-11-01	2018-11-09	Infinity Pharmaceuticals Inc	Trattamento di cancri usando modulatori di isoforme di pi3 chinasi
EP2922543B1 (en) *	2012-11-20	2017-05-24	Merck Sharp & Dohme Corp.	Substituted pyridone derivatives as pde10 inhibitors
KR101529496B1 (ko) *	2012-12-27	2015-06-22	한국과학기술원	낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드
US9481667B2 (en)	2013-03-15	2016-11-01	Infinity Pharmaceuticals, Inc.	Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
EP3004138B1 (en)	2013-06-05	2024-03-13	Bausch Health Ireland Limited	Ultra-pure agonists of guanylate cyclase c, method of making and using same
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
NZ718430A (en)	2013-10-04	2021-12-24	Infinity Pharmaceuticals Inc	Heterocyclic compounds and uses thereof
US9751888B2 (en)	2013-10-04	2017-09-05	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
KR20220038826A (ko)	2014-01-21	2022-03-29	얀센 파마슈티카 엔.브이.	대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
KR20200036063A (ko)	2014-01-21	2020-04-06	얀센 파마슈티카 엔.브이.	대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
EP3138839B1 (en) *	2014-02-14	2020-10-28	Sichuan Haisco Pharmaceutical Co., Ltd.	Pyridone or pyrimidone derivative, preparation method therefor and application thereof
DK3119397T3 (da)	2014-03-19	2022-03-28	Infinity Pharmaceuticals Inc	Heterocykliske forbindelser til anvendelse i behandling af PI3K-gamma-medierede lidelser
JP6525437B2 (ja)	2014-04-02	2019-06-05	インターミューン，インコーポレイテッド	抗線維性ピリジノン
US20150320755A1 (en)	2014-04-16	2015-11-12	Infinity Pharmaceuticals, Inc.	Combination therapies
US9708348B2 (en)	2014-10-03	2017-07-18	Infinity Pharmaceuticals, Inc.	Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
MX390633B (es)	2015-09-14	2025-03-04	Infinity Pharmaceuticals Inc	Formas solidas de derivados de isoquinolinona, proceso de fabricacion, composiciones que las contienen y metodos de uso de las mismas.
JP2017149663A (ja) *	2016-02-24	2017-08-31	株式会社Ｌｔｔバイオファーマ	過敏性腸症候群治療剤
WO2017161116A1 (en)	2016-03-17	2017-09-21	Infinity Pharmaceuticals, Inc.	Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors
WO2017214269A1 (en)	2016-06-08	2017-12-14	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
SG10201912456RA (en)	2016-06-24	2020-02-27	Infinity Pharmaceuticals Inc	Combination therapies
CN110214012B (zh) *	2017-01-20	2023-05-09	艾库斯生物科学有限公司	用于治疗癌症相关疾病的唑嘧啶
WO2018184590A1 (zh) *	2017-04-07	2018-10-11	南京明德新药研发股份有限公司	作为A 2A受体抑制剂的[1,2,4]三唑并[1,5-c]嘧啶衍生物
CN110612100B (zh) *	2017-05-05	2023-04-14	艾库斯生物科学有限公司	治疗与癌症有关疾病的喹唑啉-吡啶衍生物
US11478479B2 (en)	2018-02-16	2022-10-25	Arcus Biosciences, Inc.	Dosing with an azolopyrimidine compound
CN110240593A (zh) *	2018-03-09	2019-09-17	四川科伦博泰生物医药股份有限公司	取代芳胺化合物及其制备方法和用途
CN108314631A (zh) *	2018-04-19	2018-07-24	中国科学院昆明植物研究所	二芳基乙烯类化合物及其药物组合物和其应用
CN110655509B (zh) *	2018-06-29	2023-01-24	江苏恒瑞医药股份有限公司	2-胺基嘧啶类衍生物、其制备方法及其在医药上的应用
CN110684020B (zh) *	2018-07-05	2023-01-20	江苏恒瑞医药股份有限公司	2-胺基嘧啶类衍生物、其制备方法及其在医药上的应用
CN112423758A (zh) *	2018-07-10	2021-02-26	尼康治疗公司	腺苷受体结合化合物
WO2020011220A1 (zh) *	2018-07-12	2020-01-16	江苏恒瑞医药股份有限公司	杂芳基类衍生物、其制备方法及其在医药上的应用
CN111377873B (zh) *	2018-12-28	2023-03-28	四川科伦博泰生物医药股份有限公司	氨基嘧啶化合物及其制备方法和用途
KR20210110288A (ko) *	2018-12-28	2021-09-07	쓰촨 케룬-바이오테크 바이오파마수티컬 컴퍼니 리미티드	치환된 아릴 화합물, 및 이의 제조 방법 및 이의 용도
WO2020135195A1 (zh)	2018-12-28	2020-07-02	四川科伦博泰生物医药股份有限公司	氨基吡啶类化合物及其制备方法和用途
US10689374B1 (en)	2019-07-12	2020-06-23	United Arab Emirates University	Pyrimidine-thiazolidinone derivatives
US10702525B1 (en)	2019-09-04	2020-07-07	United Arab Emirates University	Pyrimidine derivatives as anti-diabetic agents
CA3171774C (en) *	2020-03-16	2025-05-20	Shanghai Haiyan Pharmaceutical Technology Co., Ltd.	AMINE DERIVATIVE PYRIMIDINE OR SUBSTITUTED PYRIDINE, RELATED COMPOSITION AND RELATED MEDICAL USE

Family Cites Families (57)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3029426A1 (de) *	1980-08-02	1982-03-11	Bayer Ag, 5090 Leverkusen	Gegen zwecken wirksame pour-on-formulierungen
US4725600A (en)	1984-07-13	1988-02-16	Fujisawa Pharmaceutical Co., Ltd.	Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent
FR2584925B1 (fr) *	1985-07-17	1987-11-27	Bosserelle Micheline	Composition de corps gras d'origine vegetale pour usage cosmetique
US4927813A (en) *	1988-03-08	1990-05-22	Bernstein Joel E	Method and composition for treating pediculosis capitis
JPH0252360A (ja)	1988-08-15	1990-02-21	Fujitsu Ltd	電子写真感光体
PE5591A1 (es) *	1988-12-19	1991-02-15	Lilly Co Eli	Un nuevo grupo de compuestos de macrolida
US5362634A (en) *	1989-10-30	1994-11-08	Dowelanco	Process for producing A83543 compounds
US5288483A (en) *	1990-04-18	1994-02-22	The Procter & Gamble Company	Anti-lice treatment compositions
DD294255A5 (de) *	1990-05-14	1991-09-26	Adw Forschungsstelle Fuer Chemische Toxikologie,De	Verfahren zur herstellung tetrazolylsubstituierter pyrimidinderivate
US5227163A (en) *	1991-01-18	1993-07-13	Clilco, Ltd.	Lice-repellant compositions
US5145684A (en) *	1991-01-25	1992-09-08	Sterling Drug Inc.	Surface modified drug nanoparticles
US5539089A (en) *	1991-11-08	1996-07-23	Dowelanco	A83543 aglycones and pseudoglycones
US5227295A (en) *	1991-11-08	1993-07-13	Dowelanco	Process for isolating A83543 and its components
US5202242A (en) *	1991-11-08	1993-04-13	Dowelanco	A83543 compounds and processes for production thereof
JP2613355B2 (ja)	1992-09-28	1997-05-28	協和醗酵工業株式会社	パーキンソン氏病治療剤
US5591606A (en) *	1992-11-06	1997-01-07	Dowelanco	Process for the production of A83543 compounds with Saccharopolyspora spinosa
CA2156194C (en) *	1993-03-12	2008-01-08	Jon S. Mynderse	New a83543 compounds and process for production thereof
US5795905A (en) *	1995-06-06	1998-08-18	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods relating thereto
US5935966A (en) *	1995-09-01	1999-08-10	Signal Pharmaceuticals, Inc.	Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions
EP0888335A4 (en) *	1996-03-13	2002-01-02	Smithkline Beecham Corp	NEW PYRIMIDINE COMPOUNDS AND THEIR USE IN THE TREATMENT OF CYTOKININ MEDIATOR DISEASES
US6010710A (en) *	1996-03-29	2000-01-04	Merial	Direct pour-on skin solution for antiparasitic use in cattle and sheep
US5952331A (en) *	1996-05-23	1999-09-14	Syntex (Usa) Inc.	Aryl pyrimidine derivatives
US6001981A (en) *	1996-06-13	1999-12-14	Dow Agrosciences Llc	Synthetic modification of Spinosyn compounds
FR2756177B1 (fr) *	1996-11-28	1999-01-29	Oreal	Dispersion aqueuse de vesicules resistantes a la deshydratation
TW520362B (en)	1996-12-05	2003-02-11	Amgen Inc	Substituted pyrimidine compounds and pharmaceutical composition comprising same
US6096753A (en) *	1996-12-05	2000-08-01	Amgen Inc.	Substituted pyrimidinone and pyridone compounds and methods of use
JP2002514196A (ja) *	1996-12-05	2002-05-14	アムジエン・インコーポレーテツド	置換ピリミジノンおよびピリドン化合物ならびに使用方法
EP0948497A2 (en) *	1996-12-05	1999-10-13	Amgen inc.	Substituted pyrimidine compounds and their use
DE19710435A1 (de) *	1997-03-13	1998-09-17	Hoechst Ag	Verwendung von Pyrimidinderivaten zur Prävention von Krebs allein oder in Kombination mit anderen therapeutischen Maßnahmen
US5880076A (en) *	1997-08-04	1999-03-09	Lever Brothers Company, Division Of Conopco, Inc.	Compositions comprising glycacarbamate and glycaurea compounds
US6096326A (en) *	1997-08-15	2000-08-01	Scandinavian-American Import/Export Corporation	Skin care compositions and use
JPH11188484A (ja)	1997-12-25	1999-07-13	Nkk Corp	多段研削バリ取り装置
EP1300147A1 (en) *	1998-01-05	2003-04-09	Eisai Co. Ltd	Purine compounds and adenosine A2 receptor antagonist as preventive or therapeutic agent for diabetes mellitus
JP3990061B2 (ja)	1998-01-05	2007-10-10	エーザイ・アール・アンド・ディー・マネジメント株式会社	プリン誘導体および糖尿病の予防・治療剤としてのアデノシンａ２受容体拮抗剤
US6235754B1 (en) *	1998-01-30	2001-05-22	American Cyanamid Company	Methods and compositions for protecting animals and humans against attack and infestation by arthropod and helminth parasites
DE19823397B4 (de) *	1998-05-26	2011-07-28	Bayer CropScience AG, 40789	Verwendung von Spinosynen zum Einsatz als Bodeninsektizide
ATE274510T1 (de) *	1998-06-19	2004-09-15	Chiron Corp	Glycogen synthase kinase 3 inhibitoren
US7045519B2 (en) *	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
UA65624C2 (uk) *	1998-07-02	2004-04-15	Елі Ліллі Енд Компані	Препарат для догляду за волоссям (варіанти) та спосіб боротьби з педикульозним ураженням людини із застосуванням спінозину (варіанти)
TWI241298B (en)	1998-09-25	2005-10-11	Mitsubishi Chem Corp	Pyrimidone derivatives
JP2000126489A (ja)	1998-10-21	2000-05-09	Purotonikusu Kenkyusho:Kk	糸又は布と接触するミシン用部品
NZ516260A (en)	1999-07-02	2004-08-27	Eisai Co Ltd	Fused imidazole compounds and remedies for diabetes mellitus
HRP20020673A2 (en) *	2000-02-25	2004-12-31	Hoffmann La Roche	Adenosine receptor modulators
WO2001070727A1 (en)	2000-03-23	2001-09-27	Sanofi-Synthelabo	2-(arylalkylamino)pyrimidone derivatives and 2-(heteroarylalkylamino)pyrimidone derivatives
EP1136482A1 (en)	2000-03-23	2001-09-26	Sanofi-Synthelabo	2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors
EP1136486A1 (en)	2000-03-23	2001-09-26	Sanofi-Synthelabo	2-[Indanylamino]pyrimidone and 2-[tetrahydronaphthalenylamino]pyrimidone derivatives
US7189717B2 (en) *	2000-04-26	2007-03-13	Eisai Co., Ltd.	Medicinal compositions promoting bowel movement
MXPA03001136A (es)	2000-08-11	2003-06-24	Eisai Co Ltd	Compuesto de 2-aminopiridina y uso medico del mismo.
WO2002020495A2 (en) *	2000-09-06	2002-03-14	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
AP2003002762A0 (en) *	2000-09-15	2003-03-31	Vertex Pharma	Pyrazole compounds useful as protein kinase inhibitors
WO2002024893A2 (en)	2000-09-19	2002-03-28	Chiron Corporation	CHARACTERIZATION OF THE GSK-3β PROTEIN AND METHODS OF USE THEREOF
MY130778A (en)	2001-02-09	2007-07-31	Vertex Pharma	Heterocyclic inhibitiors of erk2 and uses thereof
TWI330183B (2)	2001-10-22	2010-09-11	Eisai R&D Man Co Ltd
TWI301834B (en)	2001-10-22	2008-10-11	Eisai R&D Man Co Ltd	Pyrimidone compound and pharmaceutical composition including the same
AU2002950853A0 (en)	2002-08-19	2002-09-12	Fujisawa Pharmaceutical Co., Ltd.	Aminopyrimidine compound and pharmaceutical use thereof
US7538117B2 (en)	2005-03-21	2009-05-26	Eisai R&D Management Co., Ltd.	Crystalline and amorphous pyrimidine compounds and processes for preparing pyrimidine compounds
US7396928B2 (en)	2005-03-21	2008-07-08	Eisai R&D Management Co., Ltd.	Crystals of 5-[2-amino-4-(2-furyl) pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and processes for preparing the same

2002
- 2002-10-21 TW TW091124227A patent/TWI330183B/zh not_active IP Right Cessation
- 2002-10-22 EP EP02802050A patent/EP1439175B1/en not_active Expired - Lifetime
- 2002-10-22 IL IL16149302A patent/IL161493A0/xx unknown
- 2002-10-22 MX MXPA04003795A patent/MXPA04003795A/es active IP Right Grant
- 2002-10-22 NZ NZ532373A patent/NZ532373A/en not_active IP Right Cessation
- 2002-10-22 PL PL370274A patent/PL215572B1/pl not_active IP Right Cessation
- 2002-10-22 HU HU0401950A patent/HUP0401950A3/hu unknown
- 2002-10-22 RU RU2004115495/04A patent/RU2288227C2/ru not_active IP Right Cessation
- 2002-10-22 DE DE60239884T patent/DE60239884D1/de not_active Expired - Lifetime
- 2002-10-22 AT AT02802050T patent/ATE507217T1/de active
- 2002-10-22 EP EP10173222A patent/EP2246344A1/en not_active Withdrawn
- 2002-10-22 ES ES02802050T patent/ES2364328T3/es not_active Expired - Lifetime
- 2002-10-22 KR KR1020047005915A patent/KR100884025B1/ko not_active Expired - Fee Related
- 2002-10-22 DK DK02802050.1T patent/DK1439175T3/da active
- 2002-10-22 WO PCT/JP2002/010952 patent/WO2003035639A1/ja not_active Ceased
- 2002-10-22 JP JP2003538155A patent/JP4462930B2/ja not_active Expired - Fee Related
- 2002-10-22 CN CNB028209311A patent/CN100519549C/zh not_active Expired - Fee Related
- 2002-10-22 AU AU2002335536A patent/AU2002335536B2/en not_active Ceased
- 2002-10-22 CA CA2463284A patent/CA2463284C/en not_active Expired - Fee Related
- 2002-10-22 BR BR0213455-1A patent/BR0213455A/pt not_active IP Right Cessation
- 2002-10-22 US US10/492,905 patent/US7396836B2/en not_active Expired - Fee Related
- 2002-10-22 PT PT02802050T patent/PT1439175E/pt unknown
2004
- 2004-04-16 ZA ZA200402898A patent/ZA200402898B/xx unknown
- 2004-04-19 NO NO20041580A patent/NO327581B1/no not_active IP Right Cessation
- 2004-04-19 IL IL161493A patent/IL161493A/en not_active IP Right Cessation
2008
- 2008-03-24 US US12/054,337 patent/US20090030023A1/en not_active Abandoned
2011
- 2011-07-11 CY CY20111100672T patent/CY1112341T1/el unknown

Also Published As

Publication number	Publication date
US20050004149A1 (en)	2005-01-06
PT1439175E (pt)	2011-07-08
JPWO2003035639A1 (ja)	2005-02-10
NO327581B1 (no)	2009-08-24
CN1575290A (zh)	2005-02-02
ATE507217T1 (de)	2011-05-15
EP1439175A1 (en)	2004-07-21
KR100884025B1 (ko)	2009-02-17
CA2463284C (en)	2010-10-19
DE60239884D1 (de)	2011-06-09
ES2364328T3 (es)	2011-08-31
DK1439175T3 (da)	2011-07-18
HUP0401950A2 (hu)	2005-01-28
IL161493A0 (en)	2004-09-27
US7396836B2 (en)	2008-07-08
RU2004115495A (ru)	2005-04-10
EP2246344A1 (en)	2010-11-03
PL370274A1 (en)	2005-05-16
HUP0401950A3 (en)	2010-06-28
ZA200402898B (en)	2006-03-29
EP1439175A4 (en)	2004-12-29
CN100519549C (zh)	2009-07-29
PL215572B1 (pl)	2013-12-31
CA2463284A1 (en)	2003-05-01
KR20040053191A (ko)	2004-06-23
WO2003035639A1 (en)	2003-05-01
EP1439175B1 (en)	2011-04-27
MXPA04003795A (es)	2004-07-30
US20090030023A1 (en)	2009-01-29
CY1112341T1 (el)	2015-12-09
IL161493A (en)	2010-04-29
JP4462930B2 (ja)	2010-05-12
NZ532373A (en)	2007-02-23
NO20041580L (no)	2004-07-22
AU2002335536B2 (en)	2008-11-13
BR0213455A (pt)	2004-10-19
RU2288227C2 (ru)	2006-11-27

Legal Events

Date	Code	Title	Description
2014-06-11	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
TWI330183B (2)	2010-09-11
TWI301834B (en)	2008-10-11	Pyrimidone compound and pharmaceutical composition including the same
CN109562106B (zh)	2023-03-21	Cxcr4抑制剂及其用途
JP6994767B2 (ja)	2022-01-14	Ｃｘｃｒ４阻害剤およびその使用
DK2776397T3 (en)	2018-02-26	QUINOLINES AS FGFR CHINA MODULATORS
TWI602814B (zh)	2017-10-21	透過抑制fgfr激酶之具有抗癌性的吡啶並吡嗪衍生物化合物
JP6586104B2 (ja)	2019-10-02	５−置換インダゾール−３−カルボキサミドならびにその調製および使用の方法
ES2739348T3 (es)	2020-01-30	Pteridinas como inhibidores del FGFR
CA2853401C (en)	2022-02-15	Anticancer benzopyrazines via the inhibition of fgfr kinases
JP2021120403A (ja)	2021-08-19	一過性受容体電位ａ１イオンチャネルの阻害
CN113423707A (zh)	2021-09-21	Erk抑制剂及其用途
TW200528111A (en)	2005-09-01	Pyrido-and pyrimidopyrimidine derivatives
KR20020015060A (ko)	2002-02-27	축합 이미다졸 화합물 및 당뇨병 치료약
TW201016676A (en)	2010-05-01	Heterocyclic derivatives and methods of use thereof
TW202448473A (zh)	2024-12-16	包含ｓｏｓ１抑制劑及抗癌藥物的用於治療癌症之藥學組成物
TW201204714A (en)	2012-02-01	New compounds
CN109627239A (zh)	2019-04-16	成纤维细胞生长因子受体的抑制剂
HUP0700086A2 (en)	2007-05-29	2-aminopyridine compounds, use thereof as drugs and pharmaceutical compositions containing them
CN113773308A (zh)	2021-12-10	Rho激酶抑制剂
MX2014014112A (es)	2015-06-17	Nuevos compuestos.
CN107635986A (zh)	2018-01-26	取代的喹喔啉衍生物
TW202448871A (zh)	2024-12-16	作為sos1抑制劑之唑基吡啶嗒酮醯胺
JP2021516674A (ja)	2021-07-08	５−ヘテロアリール置換イミダゾール−３−カルボキサミドならびにその調製および使用の方法
WO2016204261A1 (ja)	2016-12-22	アミノピラゾール誘導体
JP2022506289A (ja)	2022-01-17	インダゾールキナーゼ阻害剤及びその使用