CA2425283A1 - Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors - Google Patents

Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors Download PDF

Info

Publication number: CA2425283A1
Authority: CA; Canada
Prior art keywords: alkyl; group; pyridin; spiro; triaza
Prior art date: 2000-10-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002425283A

Other languages

English (en)

French (fr)

Inventor

Brian Scott Bronk

Mark Carl Noe

Martin James Wythes

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Individual

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.)

2000-10-26

Filing date

2001-10-23

Publication date

2002-05-02

2001-10-23 Application filed by Individual filed Critical Individual

2002-05-02 Publication of CA2425283A1 publication Critical patent/CA2425283A1/en

Status Abandoned legal-status Critical Current

Links

239000003475 metalloproteinase inhibitor Substances 0.000 title abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 96
238000000034 method Methods 0.000 claims abstract description 29
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 231
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 79
229910052760 oxygen Inorganic materials 0.000 claims description 79
239000001301 oxygen Substances 0.000 claims description 79
125000000217 alkyl group Chemical group 0.000 claims description 76
125000001424 substituent group Chemical group 0.000 claims description 56
229910052799 carbon Inorganic materials 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 50
239000001257 hydrogen Substances 0.000 claims description 50
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 42
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
239000011593 sulfur Substances 0.000 claims description 33
229910052717 sulfur Inorganic materials 0.000 claims description 33
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
208000035475 disorder Diseases 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 25
230000005764 inhibitory process Effects 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 21
108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 21
229920001774 Perfluoroether Polymers 0.000 claims description 21
229910052794 bromium Inorganic materials 0.000 claims description 21
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 12
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
210000004185 liver Anatomy 0.000 claims description 7
206010020751 Hypersensitivity Diseases 0.000 claims description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
208000018631 connective tissue disease Diseases 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
208000017169 kidney disease Diseases 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
208000023504 respiratory system disease Diseases 0.000 claims description 6
208000017520 skin disease Diseases 0.000 claims description 6
208000024172 Cardiovascular disease Diseases 0.000 claims description 5
208000035473 Communicable disease Diseases 0.000 claims description 5
208000012895 Gastric disease Diseases 0.000 claims description 5
208000026935 allergic disease Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
208000030533 eye disease Diseases 0.000 claims description 5
208000019423 liver disease Diseases 0.000 claims description 5
208000030159 metabolic disease Diseases 0.000 claims description 5
230000009933 reproductive health Effects 0.000 claims description 5
208000000453 Skin Neoplasms Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
FPGLDNOEDDIHDV-UHFFFAOYSA-N 1-[6-(4-bromophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 FPGLDNOEDDIHDV-UHFFFAOYSA-N 0.000 claims description 3
COHKACKHFIJNRE-UHFFFAOYSA-N 1-[6-[4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2OC=NN=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O COHKACKHFIJNRE-UHFFFAOYSA-N 0.000 claims description 3
XTGSXSLCZLEGOR-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 XTGSXSLCZLEGOR-UHFFFAOYSA-N 0.000 claims description 2
PPPWURMAIMIOFT-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(CN3N=CC=C3)=CC=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O PPPWURMAIMIOFT-UHFFFAOYSA-N 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
KPXPFHIVDNBNJV-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]butanamide Chemical compound C1=CC(CNC(=O)CCC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 KPXPFHIVDNBNJV-UHFFFAOYSA-N 0.000 claims description 2
ZYRVUKSWVPEYJR-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)CCC11C(=O)NC(=O)NC1=O ZYRVUKSWVPEYJR-UHFFFAOYSA-N 0.000 claims description 2
NEAOVPZGCKZONB-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]pentanamide Chemical compound C1=CC(CNC(=O)CCCC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 NEAOVPZGCKZONB-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 14
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims 11
125000000041 C6-C10 aryl group Chemical group 0.000 claims 9
208000015114 central nervous system disease Diseases 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
229940080818 propionamide Drugs 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 8
201000011510 cancer Diseases 0.000 abstract description 4
206010061218 Inflammation Diseases 0.000 abstract description 3
230000004054 inflammatory process Effects 0.000 abstract description 3
-1 i.e. Chemical class 0.000 description 102
125000004076 pyridyl group Chemical group 0.000 description 73
239000002585 base Substances 0.000 description 64
125000001072 heteroaryl group Chemical group 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
239000003112 inhibitor Substances 0.000 description 61
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
239000002904 solvent Substances 0.000 description 49
102000004190 Enzymes Human genes 0.000 description 48
108090000790 Enzymes Proteins 0.000 description 48
229940088598 enzyme Drugs 0.000 description 48
239000000203 mixture Substances 0.000 description 48
125000003373 pyrazinyl group Chemical group 0.000 description 48
125000002098 pyridazinyl group Chemical group 0.000 description 46
125000000714 pyrimidinyl group Chemical group 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 43
238000003556 assay Methods 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000011575 calcium Substances 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
238000002360 preparation method Methods 0.000 description 35
125000003118 aryl group Chemical group 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
125000005843 halogen group Chemical group 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
125000001715 oxadiazolyl group Chemical group 0.000 description 27
125000003226 pyrazolyl group Chemical group 0.000 description 27
125000003545 alkoxy group Chemical group 0.000 description 26
125000002883 imidazolyl group Chemical group 0.000 description 26
108010002352 Interleukin-1 Proteins 0.000 description 25
102000000589 Interleukin-1 Human genes 0.000 description 25
125000001786 isothiazolyl group Chemical group 0.000 description 25
125000000842 isoxazolyl group Chemical group 0.000 description 25
125000002971 oxazolyl group Chemical group 0.000 description 24
102100027995 Collagenase 3 Human genes 0.000 description 23
108050005238 Collagenase 3 Proteins 0.000 description 23
239000000243 solution Substances 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 20
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 20
239000000758 substrate Substances 0.000 description 20
102000029816 Collagenase Human genes 0.000 description 19
108060005980 Collagenase Proteins 0.000 description 19
230000000694 effects Effects 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
238000007792 addition Methods 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
229960002424 collagenase Drugs 0.000 description 17
238000010790 dilution Methods 0.000 description 17
239000012895 dilution Substances 0.000 description 17
239000003814 drug Substances 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 16
229910052791 calcium Inorganic materials 0.000 description 16
125000001309 chloro group Chemical group Cl* 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
229940079593 drug Drugs 0.000 description 14
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
210000000845 cartilage Anatomy 0.000 description 13
238000005481 NMR spectroscopy Methods 0.000 description 12
229920001436 collagen Polymers 0.000 description 12
108010035532 Collagen Proteins 0.000 description 11
102000008186 Collagen Human genes 0.000 description 11
102000004142 Trypsin Human genes 0.000 description 11
108090000631 Trypsin Proteins 0.000 description 11
239000012131 assay buffer Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
239000006188 syrup Substances 0.000 description 11
235000020357 syrup Nutrition 0.000 description 11
239000012588 trypsin Substances 0.000 description 11
125000001246 bromo group Chemical group Br* 0.000 description 10
125000000753 cycloalkyl group Chemical group 0.000 description 10
229940002612 prodrug Drugs 0.000 description 10
239000000651 prodrug Substances 0.000 description 10
239000011347 resin Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
239000011550 stock solution Substances 0.000 description 10
239000004202 carbamide Substances 0.000 description 9
210000003169 central nervous system Anatomy 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
125000004043 oxo group Chemical group O=* 0.000 description 9
238000003756 stirring Methods 0.000 description 9
150000003512 tertiary amines Chemical class 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
102100030416 Stromelysin-1 Human genes 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
239000002798 polar solvent Substances 0.000 description 8
125000000168 pyrrolyl group Chemical group 0.000 description 8
239000007787 solid Substances 0.000 description 8
VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 7
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 7
101710108790 Stromelysin-1 Proteins 0.000 description 7
239000007983 Tris buffer Substances 0.000 description 7
HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 7
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 7
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 7
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 7
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 7
201000010099 disease Diseases 0.000 description 7
125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 7
125000002541 furyl group Chemical group 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 7
125000002346 iodo group Chemical group I* 0.000 description 7
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 7
238000002534 molecular mass spectrometry Methods 0.000 description 7
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 7
238000005580 one pot reaction Methods 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 7
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 7
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 7
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
125000001113 thiadiazolyl group Chemical group 0.000 description 7
125000000335 thiazolyl group Chemical group 0.000 description 7
125000001544 thienyl group Chemical group 0.000 description 7
125000004306 triazinyl group Chemical group 0.000 description 7
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 6
102100026802 72 kDa type IV collagenase Human genes 0.000 description 6
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 6
102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 6
102000005741 Metalloproteases Human genes 0.000 description 6
108010006035 Metalloproteases Proteins 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 6
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 6
125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
125000003838 furazanyl group Chemical group 0.000 description 6
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 6
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 6
125000001041 indolyl group Chemical group 0.000 description 6
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 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
231100000252 nontoxic Toxicity 0.000 description 6
230000003000 nontoxic effect Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
125000003831 tetrazolyl group Chemical group 0.000 description 6
125000001425 triazolyl group Chemical group 0.000 description 6
NCQJBPXXRXOIJD-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoic acid Chemical compound C1=CC=CC2=CC(C(CC(O)=O)NC(=O)OC(C)(C)C)=CC=C21 NCQJBPXXRXOIJD-UHFFFAOYSA-N 0.000 description 5
101710151806 72 kDa type IV collagenase Proteins 0.000 description 5
102000013382 Gelatinases Human genes 0.000 description 5
108010026132 Gelatinases Proteins 0.000 description 5
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 5
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 5
241001465754 Metazoa Species 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000001476 alcoholic effect Effects 0.000 description 5
150000004703 alkoxides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
239000003636 conditioned culture medium Substances 0.000 description 5
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 5
230000005284 excitation Effects 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
229960002591 hydroxyproline Drugs 0.000 description 5
239000002609 medium Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
241000283690 Bos taurus Species 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
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 4
229940124761 MMP inhibitor Drugs 0.000 description 4
102100030417 Matrilysin Human genes 0.000 description 4
108090000855 Matrilysin Proteins 0.000 description 4
108010076557 Matrix Metalloproteinase 14 Proteins 0.000 description 4
102100030216 Matrix metalloproteinase-14 Human genes 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
210000001188 articular cartilage Anatomy 0.000 description 4
KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
210000001612 chondrocyte Anatomy 0.000 description 4
230000011382 collagen catabolic process Effects 0.000 description 4
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 4
230000006378 damage Effects 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
CJKVSXOYRXHLJP-UHFFFAOYSA-N diethyl 1-[6-(4-formylphenoxy)pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1C(C=N1)=CC=C1OC1=CC=C(C=O)C=C1 CJKVSXOYRXHLJP-UHFFFAOYSA-N 0.000 description 4
230000029087 digestion Effects 0.000 description 4
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
238000011534 incubation Methods 0.000 description 4
238000005567 liquid scintillation counting Methods 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
210000002184 nasal cartilage Anatomy 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
201000008482 osteoarthritis Diseases 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
125000003386 piperidinyl group Chemical group 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000012360 testing method Methods 0.000 description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 4
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
BQTGEPHGOSFJKZ-UHFFFAOYSA-N 6-(4-bromophenoxy)pyridin-3-amine Chemical compound N1=CC(N)=CC=C1OC1=CC=C(Br)C=C1 BQTGEPHGOSFJKZ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
102000000503 Collagen Type II Human genes 0.000 description 3
108010041390 Collagen Type II Proteins 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
239000012981 Hank's balanced salt solution Substances 0.000 description 3
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
102100027998 Macrophage metalloelastase Human genes 0.000 description 3
101710187853 Macrophage metalloelastase Proteins 0.000 description 3
108090000526 Papain Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000004365 Protease Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
102100040247 Tumor necrosis factor Human genes 0.000 description 3
208000025865 Ulcer Diseases 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
239000000556 agonist Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000539 amino acid group Chemical group 0.000 description 3
208000007474 aortic aneurysm Diseases 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000000872 buffer Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000002442 collagenase inhibitor Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229940111134 coxibs Drugs 0.000 description 3
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229920002674 hyaluronan Polymers 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
208000002780 macular degeneration Diseases 0.000 description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229940055729 papain Drugs 0.000 description 3
235000019834 papain Nutrition 0.000 description 3
125000004193 piperazinyl group Chemical group 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
239000003880 polar aprotic solvent Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000002285 radioactive effect Effects 0.000 description 3
206010039073 rheumatoid arthritis Diseases 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 2
OSYNXIZIEQNWIC-UHFFFAOYSA-N 4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound C=1C=C(OC=2C=CC(=CC=2)C#N)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O OSYNXIZIEQNWIC-UHFFFAOYSA-N 0.000 description 2
HZLQBILZJFDZRC-UHFFFAOYSA-N 4-[5-[2,2-bis(ethoxycarbonyl)-5-oxopyrrolidin-1-yl]pyridin-2-yl]oxybenzoic acid Chemical compound CCOC(=O)C1(C(=O)OCC)CCC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C(O)=O)C=C1 HZLQBILZJFDZRC-UHFFFAOYSA-N 0.000 description 2
GTZIJWRUYJNVLH-UHFFFAOYSA-N 7-[6-(4-fluorophenoxy)pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCCC2=O)C=N1 GTZIJWRUYJNVLH-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 2
102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 2
101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229940127291 Calcium channel antagonist Drugs 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
102000012422 Collagen Type I Human genes 0.000 description 2
108010022452 Collagen Type I Proteins 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
206010060820 Joint injury Diseases 0.000 description 2
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
101150014058 MMP1 gene Proteins 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
102100030219 Matrix metalloproteinase-17 Human genes 0.000 description 2
108090000585 Matrix metalloproteinase-17 Proteins 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
102100030411 Neutrophil collagenase Human genes 0.000 description 2
101710118230 Neutrophil collagenase Proteins 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
208000001132 Osteoporosis Diseases 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
108010067787 Proteoglycans Proteins 0.000 description 2
102000016611 Proteoglycans Human genes 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
201000001263 Psoriatic Arthritis Diseases 0.000 description 2
208000036824 Psoriatic arthropathy Diseases 0.000 description 2
208000017442 Retinal disease Diseases 0.000 description 2
206010038923 Retinopathy Diseases 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
108091006463 SLC25A24 Proteins 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
208000006011 Stroke Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
206010064930 age-related macular degeneration Diseases 0.000 description 2
239000000783 alginic acid Substances 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
229960001126 alginic acid Drugs 0.000 description 2
150000004781 alginic acids Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000033115 angiogenesis Effects 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229960004436 budesonide Drugs 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
235000011148 calcium chloride Nutrition 0.000 description 2
229960000590 celecoxib Drugs 0.000 description 2
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 2
206010008118 cerebral infarction Diseases 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
208000002849 chondrocalcinosis Diseases 0.000 description 2
108700004333 collagenase 1 Proteins 0.000 description 2
238000003271 compound fluorescence assay Methods 0.000 description 2
210000002808 connective tissue Anatomy 0.000 description 2
125000000000 cycloalkoxy group Chemical group 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
XVTCIMPCUQKYND-UHFFFAOYSA-N diethyl 1-[6-(4-bromophenoxy)pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1C(C=N1)=CC=C1OC1=CC=C(Br)C=C1 XVTCIMPCUQKYND-UHFFFAOYSA-N 0.000 description 2
ITGPSFRTXTUTDD-UHFFFAOYSA-N diethyl 1-[6-(4-ethenylphenoxy)pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1C(C=N1)=CC=C1OC1=CC=C(C=C)C=C1 ITGPSFRTXTUTDD-UHFFFAOYSA-N 0.000 description 2
MSTUYXXALDFMIX-UHFFFAOYSA-N diethyl 1-[6-[4-(hydrazinecarbonyl)phenoxy]pyridin-3-yl]-5-oxopyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCC(=O)N1C(C=N1)=CC=C1OC1=CC=C(C(=O)NN)C=C1 MSTUYXXALDFMIX-UHFFFAOYSA-N 0.000 description 2
HNQQMEJRDKZDJH-UHFFFAOYSA-N diethyl 1-[6-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenoxy]pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1C(C=N1)=CC=C1OC1=CC=C(CNC(=O)OC(C)(C)C)C=C1 HNQQMEJRDKZDJH-UHFFFAOYSA-N 0.000 description 2
ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
229960004945 etoricoxib Drugs 0.000 description 2
MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
229960002870 gabapentin Drugs 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
229940050410 gluconate Drugs 0.000 description 2
150000002302 glucosamines Chemical class 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
229940102223 injectable solution Drugs 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
239000008101 lactose Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 2
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 2
229960000485 methotrexate Drugs 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
210000001616 monocyte Anatomy 0.000 description 2
210000005087 mononuclear cell Anatomy 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
210000000214 mouth Anatomy 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
230000003349 osteoarthritic effect Effects 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
208000033808 peripheral neuropathy Diseases 0.000 description 2
210000003800 pharynx Anatomy 0.000 description 2
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
229960005235 piperonyl butoxide Drugs 0.000 description 2
239000000106 platelet aggregation inhibitor Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000013641 positive control Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229960000371 rofecoxib Drugs 0.000 description 2
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
125000004568 thiomorpholinyl group Chemical group 0.000 description 2
238000012384 transportation and delivery Methods 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
230000036269 ulceration Effects 0.000 description 2
229960002004 valdecoxib Drugs 0.000 description 2
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 2
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
NDQQRRVKUBPTHQ-QBIQUQHTSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO NDQQRRVKUBPTHQ-QBIQUQHTSA-N 0.000 description 1
RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
LQGXRZXTJAMADW-UHFFFAOYSA-N 1-(4-pyridin-4-yloxyphenyl)-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CN=CC=2)C=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O LQGXRZXTJAMADW-UHFFFAOYSA-N 0.000 description 1
FBYIKMHADVVBPS-UHFFFAOYSA-N 1-[6-(1h-indazol-5-yloxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=C3C=NNC3=CC=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O FBYIKMHADVVBPS-UHFFFAOYSA-N 0.000 description 1
JIUGEMBLADFQGC-UHFFFAOYSA-N 1-[6-(3-fluorophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound FC1=CC=CC(OC=2N=CC(=CC=2)N2C3(C(NC(=O)NC3=O)=O)CCC2=O)=C1 JIUGEMBLADFQGC-UHFFFAOYSA-N 0.000 description 1
LMCACCNYHDRTKB-UHFFFAOYSA-N 1-[6-(4-ethylphenoxy)pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,4,6,8,10-pentone Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)C(=O)NC2=O)C=N1 LMCACCNYHDRTKB-UHFFFAOYSA-N 0.000 description 1
YPJVMWJVUHFQOY-UHFFFAOYSA-N 1-[6-(4-ethylphenoxy)pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CNC2=O)C=N1 YPJVMWJVUHFQOY-UHFFFAOYSA-N 0.000 description 1
HXLWZZSEFNRHAP-UHFFFAOYSA-N 1-[6-(4-ethylphenoxy)pyridin-3-yl]-1,3,8,10-tetrazaspiro[5.5]undecane-2,7,9,11-tetrone Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCNC2=O)C=N1 HXLWZZSEFNRHAP-UHFFFAOYSA-N 0.000 description 1
XYFYCCJPDPFJEF-UHFFFAOYSA-N 1-[6-(4-ethylphenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-6,8,10-trione Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2)C=N1 XYFYCCJPDPFJEF-UHFFFAOYSA-N 0.000 description 1
KATZCRSWAYXZLF-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,4,6,8,10-pentone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)C(=O)NC2=O)C=N1 KATZCRSWAYXZLF-UHFFFAOYSA-N 0.000 description 1
DJCAIEAYZGFFDA-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CNC2=O)C=N1 DJCAIEAYZGFFDA-UHFFFAOYSA-N 0.000 description 1
FJLOMKPONQHSNC-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,3,8,10-tetrazaspiro[5.5]undecane-2,7,9,11-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCNC2=O)C=N1 FJLOMKPONQHSNC-UHFFFAOYSA-N 0.000 description 1
AOSUTMRBALZLRS-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-6,8,10-trione Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2)C=N1 AOSUTMRBALZLRS-UHFFFAOYSA-N 0.000 description 1
HOWQCIYWRLCJTC-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-3-methyl-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)N=CC=1N1C(=O)C(C)CC21C(=O)NC(=O)NC2=O HOWQCIYWRLCJTC-UHFFFAOYSA-N 0.000 description 1
NYOGYVBCSKKNIS-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,4,6,8,10-pentone Chemical compound C=1C=C(OC=2C=CC(CN3N=CC=C3)=CC=2)N=CC=1N1C(=O)NC(=O)C21C(=O)NC(=O)NC2=O NYOGYVBCSKKNIS-UHFFFAOYSA-N 0.000 description 1
NGEODMTXZQKNGH-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,3,7,9-tetrazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(CN3N=CC=C3)=CC=2)N=CC=1N1C(=O)NCC21C(=O)NC(=O)NC2=O NGEODMTXZQKNGH-UHFFFAOYSA-N 0.000 description 1
LGTRSXSSORAIFX-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,3,8,10-tetrazaspiro[5.5]undecane-2,7,9,11-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(CN4N=CC=C4)=CC=3)=CC=2)C(=O)NCC1 LGTRSXSSORAIFX-UHFFFAOYSA-N 0.000 description 1
DVDYHMAYQYKATK-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-6,8,10-trione Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(CN4N=CC=C4)=CC=3)=CC=2)CCC1 DVDYHMAYQYKATK-UHFFFAOYSA-N 0.000 description 1
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
OZGMODDEIHYPRY-UHFFFAOYSA-N 2-bromopropanoyl chloride Chemical compound CC(Br)C(Cl)=O OZGMODDEIHYPRY-UHFFFAOYSA-N 0.000 description 1
BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
VNVNZKCCDVFGAP-NMFAMCKASA-N 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol 2,3-dihydroxybutanedioic acid Chemical compound OC(C(O)C(O)=O)C(O)=O.CC(C)(C)NC[C@H](O)c1ccc(O)c(CO)c1.CC(C)(C)NC[C@H](O)c1ccc(O)c(CO)c1 VNVNZKCCDVFGAP-NMFAMCKASA-N 0.000 description 1
QIAMFWBMOSTFOJ-UHFFFAOYSA-N 4-[5-(1,3,5,8-tetraoxo-2,4,7-triazaspiro[5.5]undecan-7-yl)pyridin-2-yl]oxybenzonitrile Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(=CC=3)C#N)=CC=2)C(=O)CCC1 QIAMFWBMOSTFOJ-UHFFFAOYSA-N 0.000 description 1
BXVNHZGLZJWTAL-UHFFFAOYSA-N 4-[5-(2,4,6,8,10-pentaoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound C=1C=C(OC=2C=CC(=CC=2)C#N)N=CC=1N1C(=O)NC(=O)C21C(=O)NC(=O)NC2=O BXVNHZGLZJWTAL-UHFFFAOYSA-N 0.000 description 1
QKSJYYGTHFRNDY-UHFFFAOYSA-N 4-[5-(2,6,8,10-tetraoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound C=1C=C(OC=2C=CC(=CC=2)C#N)N=CC=1N1C(=O)NCC21C(=O)NC(=O)NC2=O QKSJYYGTHFRNDY-UHFFFAOYSA-N 0.000 description 1
ZIWNZGREJQZNDC-UHFFFAOYSA-N 4-[5-(2,7,9,11-tetraoxo-1,3,8,10-tetrazaspiro[5.5]undecan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(=CC=3)C#N)=CC=2)C(=O)NCC1 ZIWNZGREJQZNDC-UHFFFAOYSA-N 0.000 description 1
DYPFKJINKIXUTI-UHFFFAOYSA-N 4-[5-(6,8,10-trioxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(=CC=3)C#N)=CC=2)CCC1 DYPFKJINKIXUTI-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 description 1
DXONOTKQLTXSIT-UHFFFAOYSA-N 7-(4-pyridin-4-yloxyphenyl)-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=CC(OC=3C=CN=CC=3)=CC=2)C(=O)CCC1 DXONOTKQLTXSIT-UHFFFAOYSA-N 0.000 description 1
FJIPAXGDMBWHGS-UHFFFAOYSA-N 7-(5-pyridin-4-yloxypyridin-2-yl)-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2N=CC(OC=3C=CN=CC=3)=CC=2)C(=O)CCC1 FJIPAXGDMBWHGS-UHFFFAOYSA-N 0.000 description 1
WSNUFMXQTAIUQQ-UHFFFAOYSA-N 7-(6-pyridin-4-yloxypyridin-3-yl)-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CN=CC=3)=CC=2)C(=O)CCC1 WSNUFMXQTAIUQQ-UHFFFAOYSA-N 0.000 description 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
CMSIGUABCOSFDG-UHFFFAOYSA-N 7-[4-[4-(1,3,4-oxadiazol-2-yl)phenoxy]phenyl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=CC(OC=3C=CC(=CC=3)C=3OC=NN=3)=CC=2)C(=O)CCC1 CMSIGUABCOSFDG-UHFFFAOYSA-N 0.000 description 1
HSUOULXQRDRMQY-UHFFFAOYSA-N 7-[6-(4-ethylphenoxy)pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCCC2=O)C=N1 HSUOULXQRDRMQY-UHFFFAOYSA-N 0.000 description 1
BEQMUIVCWGFHNH-UHFFFAOYSA-N 7-[6-[2-fluoro-4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound FC1=CC(C=2OC=NN=2)=CC=C1OC(N=C1)=CC=C1N1C(=O)CCCC11C(=O)NC(=O)NC1=O BEQMUIVCWGFHNH-UHFFFAOYSA-N 0.000 description 1
GVFYXDOFKMWEBS-UHFFFAOYSA-N 7-[6-[3-fluoro-4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound C=1C=C(C=2OC=NN=2)C(F)=CC=1OC(N=C1)=CC=C1N1C(=O)CCCC11C(=O)NC(=O)NC1=O GVFYXDOFKMWEBS-UHFFFAOYSA-N 0.000 description 1
MMHCRRYYQMFIMI-UHFFFAOYSA-N 7-[6-[3-methyl-4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound C=1C=C(C=2OC=NN=2)C(C)=CC=1OC(N=C1)=CC=C1N1C(=O)CCCC11C(=O)NC(=O)NC1=O MMHCRRYYQMFIMI-UHFFFAOYSA-N 0.000 description 1
MBLKCNZSYOUJPJ-UHFFFAOYSA-N 7-[6-[4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(=CC=3)C=3OC=NN=3)=CC=2)C(=O)CCC1 MBLKCNZSYOUJPJ-UHFFFAOYSA-N 0.000 description 1
MQFXYGLYULHZII-UHFFFAOYSA-N 7-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound O=C1NC(=O)NC(=O)C11N(C=2C=NC(OC=3C=CC(CN4N=CC=C4)=CC=3)=CC=2)C(=O)CCC1 MQFXYGLYULHZII-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
239000005541 ACE inhibitor Substances 0.000 description 1
108091022885 ADAM Proteins 0.000 description 1
102000029791 ADAM Human genes 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
206010048998 Acute phase reaction Diseases 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
102100036601 Aggrecan core protein Human genes 0.000 description 1
108010067219 Aggrecans Proteins 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
229940124810 Alzheimer's drug Drugs 0.000 description 1
102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
208000003120 Angiofibroma Diseases 0.000 description 1
102400000068 Angiostatin Human genes 0.000 description 1
108010079709 Angiostatins Proteins 0.000 description 1
229940127398 Angiotensin 2 Receptor Antagonists Drugs 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
206010053555 Arthritis bacterial Diseases 0.000 description 1
206010003267 Arthritis reactive Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
206010006895 Cachexia Diseases 0.000 description 1
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 description 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
206010011017 Corneal graft rejection Diseases 0.000 description 1
208000028006 Corneal injury Diseases 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
206010011985 Decubitus ulcer Diseases 0.000 description 1
208000016192 Demyelinating disease Diseases 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
240000001879 Digitalis lutea Species 0.000 description 1
ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
206010013908 Dysfunctional uterine bleeding Diseases 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
102100040278 E3 ubiquitin-protein ligase RNF19A Human genes 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
238000008157 ELISA kit Methods 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
201000009273 Endometriosis Diseases 0.000 description 1
102400001047 Endostatin Human genes 0.000 description 1
108010079505 Endostatins Proteins 0.000 description 1
241000792859 Enema Species 0.000 description 1
206010014989 Epidermolysis bullosa Diseases 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
108010008165 Etanercept Proteins 0.000 description 1
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
208000022461 Glomerular disease Diseases 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
208000002250 Hematologic Neoplasms Diseases 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000768078 Homo sapiens Amine oxidase [flavin-containing] B Proteins 0.000 description 1
101001011896 Homo sapiens Matrix metalloproteinase-19 Proteins 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
108060003951 Immunoglobulin Proteins 0.000 description 1
206010062016 Immunosuppression Diseases 0.000 description 1
208000004575 Infectious Arthritis Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
206010022489 Insulin Resistance Diseases 0.000 description 1
102000019223 Interleukin-1 receptor Human genes 0.000 description 1
108050006617 Interleukin-1 receptor Proteins 0.000 description 1
102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
208000012659 Joint disease Diseases 0.000 description 1
208000003456 Juvenile Arthritis Diseases 0.000 description 1
206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
201000002287 Keratoconus Diseases 0.000 description 1
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 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
108010009384 L-Iditol 2-Dehydrogenase Proteins 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
UCUNFLYVYCGDHP-BYPYZUCNSA-N L-methionine sulfone Chemical compound CS(=O)(=O)CC[C@H](N)C(O)=O UCUNFLYVYCGDHP-BYPYZUCNSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
108010007859 Lisinopril Proteins 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
108010075654 MAP Kinase Kinase Kinase 1 Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
102000055008 Matrilin Proteins Human genes 0.000 description 1
108010072582 Matrilin Proteins Proteins 0.000 description 1
108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 1
102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 1
108010016160 Matrix Metalloproteinase 3 Proteins 0.000 description 1
102100030201 Matrix metalloproteinase-15 Human genes 0.000 description 1
108090000560 Matrix metalloproteinase-15 Proteins 0.000 description 1
102100030200 Matrix metalloproteinase-16 Human genes 0.000 description 1
108090000561 Matrix metalloproteinase-16 Proteins 0.000 description 1
102100030218 Matrix metalloproteinase-19 Human genes 0.000 description 1
108090000587 Matrix metalloproteinase-19 Proteins 0.000 description 1
102000004055 Matrix metalloproteinase-19 Human genes 0.000 description 1
102100029693 Matrix metalloproteinase-20 Human genes 0.000 description 1
108090000609 Matrix metalloproteinase-20 Proteins 0.000 description 1
102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 1
102000003843 Metalloendopeptidases Human genes 0.000 description 1
108090000131 Metalloendopeptidases Proteins 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
206010027514 Metrorrhagia Diseases 0.000 description 1
BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
102100033115 Mitogen-activated protein kinase kinase kinase 1 Human genes 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
208000034578 Multiple myelomas Diseases 0.000 description 1
206010062207 Mycobacterial infection Diseases 0.000 description 1
JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 description 1
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
208000010191 Osteitis Deformans Diseases 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
208000027868 Paget disease Diseases 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
206010035226 Plasma cell myeloma Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
208000003107 Premature Rupture Fetal Membranes Diseases 0.000 description 1
208000004210 Pressure Ulcer Diseases 0.000 description 1
208000024777 Prion disease Diseases 0.000 description 1
208000002158 Proliferative Vitreoretinopathy Diseases 0.000 description 1
RBQOQRRFDPXAGN-UHFFFAOYSA-N Propentofylline Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCC RBQOQRRFDPXAGN-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
206010063837 Reperfusion injury Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
206010038933 Retinopathy of prematurity Diseases 0.000 description 1
206010038934 Retinopathy proliferative Diseases 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
206010039705 Scleritis Diseases 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
208000021386 Sjogren Syndrome Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
102100026974 Sorbitol dehydrogenase Human genes 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
102100028848 Stromelysin-2 Human genes 0.000 description 1
101710108792 Stromelysin-2 Proteins 0.000 description 1
102100028847 Stromelysin-3 Human genes 0.000 description 1
108050005271 Stromelysin-3 Proteins 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
229940100389 Sulfonylurea Drugs 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
239000000150 Sympathomimetic Substances 0.000 description 1
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
229940123464 Thiazolidinedione Drugs 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
229940122618 Trypsin inhibitor Drugs 0.000 description 1
101710162629 Trypsin inhibitor Proteins 0.000 description 1
108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
206010064390 Tumour invasion Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
206010064996 Ulcerative keratitis Diseases 0.000 description 1
241000700605 Viruses Species 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
101001011890 Xenopus laevis Matrix metalloproteinase-18 Proteins 0.000 description 1
YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229960000446 abciximab Drugs 0.000 description 1
208000002223 abdominal aortic aneurysm Diseases 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
229960002632 acarbose Drugs 0.000 description 1
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
GLRAHDCHUZLKKC-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid;hydrate Chemical compound O.CC#N.OC(=O)C(F)(F)F GLRAHDCHUZLKKC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000004658 acute-phase response Effects 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000000464 adrenergic agent Substances 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
108010003059 aggrecanase Proteins 0.000 description 1
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
239000003288 aldose reductase inhibitor Substances 0.000 description 1
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000001336 alkenes Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
229960000528 amlodipine Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003872 anastomosis Effects 0.000 description 1
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000007131 anti Alzheimer effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
229940035678 anti-parkinson drug Drugs 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
229940111136 antiinflammatory and antirheumatic drug fenamates Drugs 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 1
229960005207 auranofin Drugs 0.000 description 1
229960001671 azapropazone Drugs 0.000 description 1
WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
150000007656 barbituric acids Chemical class 0.000 description 1
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
229940092705 beclomethasone Drugs 0.000 description 1
230000008901 benefit Effects 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
239000002876 beta blocker Substances 0.000 description 1
229940097320 beta blocking agent Drugs 0.000 description 1
229940000635 beta-alanine Drugs 0.000 description 1
125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000004166 bioassay Methods 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
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
230000009400 cancer invasion Effects 0.000 description 1
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
229960000830 captopril Drugs 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
229960003115 certolizumab pegol Drugs 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
229960001803 cetirizine Drugs 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
101150087654 chrnd gene Proteins 0.000 description 1
208000019069 chronic childhood arthritis Diseases 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000007882 cirrhosis Effects 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
229960002173 citrulline Drugs 0.000 description 1
235000013477 citrulline Nutrition 0.000 description 1
229960004022 clotrimazole Drugs 0.000 description 1
VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000019771 cognition Effects 0.000 description 1
230000036569 collagen breakdown Effects 0.000 description 1
230000000112 colonic effect Effects 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
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 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
239000000850 decongestant Substances 0.000 description 1
229940124581 decongestants Drugs 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
229960001259 diclofenac Drugs 0.000 description 1
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
FZXJBOWSXKMFEP-UHFFFAOYSA-N diethyl 1-[6-(4-cyanophenoxy)pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1C(C=N1)=CC=C1OC1=CC=C(C#N)C=C1 FZXJBOWSXKMFEP-UHFFFAOYSA-N 0.000 description 1
FLYWOROEBPFCIJ-UHFFFAOYSA-N diethyl 1-[6-[4-(bromomethyl)phenoxy]pyridin-3-yl]-5-oxopyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCC(=O)N1C(C=N1)=CC=C1OC1=CC=C(CBr)C=C1 FLYWOROEBPFCIJ-UHFFFAOYSA-N 0.000 description 1
MBUCMQOSNOFBPA-UHFFFAOYSA-N diethyl 5-oxo-1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCC(=O)N1C(C=N1)=CC=C1OC(C=C1)=CC=C1CN1N=CC=C1 MBUCMQOSNOFBPA-UHFFFAOYSA-N 0.000 description 1
DHWOXCBGAJCELU-UHFFFAOYSA-N diethyl pyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCN1 DHWOXCBGAJCELU-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
230000010339 dilation Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
NEMOJKROKMMQBQ-UHFFFAOYSA-N dimethyl 2-bromopropanedioate Chemical compound COC(=O)C(Br)C(=O)OC NEMOJKROKMMQBQ-UHFFFAOYSA-N 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
229960003668 docetaxel Drugs 0.000 description 1
229960003530 donepezil Drugs 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
239000000221 dopamine uptake inhibitor Substances 0.000 description 1
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
229960001389 doxazosin Drugs 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
229950004203 droloxifene Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
210000003372 endocrine gland Anatomy 0.000 description 1
210000004696 endometrium Anatomy 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229960000403 etanercept Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
208000024519 eye neoplasm Diseases 0.000 description 1
229960001419 fenoprofen Drugs 0.000 description 1
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
229960003592 fexofenadine Drugs 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
230000003176 fibrotic effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229960004884 fluconazole Drugs 0.000 description 1
RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
229960002714 fluticasone Drugs 0.000 description 1
MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229960002490 fosinopril Drugs 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
208000024386 fungal infectious disease Diseases 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000001879 gelation Methods 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
229960004346 glimepiride Drugs 0.000 description 1
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
229960001381 glipizide Drugs 0.000 description 1
231100000852 glomerular disease Toxicity 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000003316 glycosidase inhibitor Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
208000010758 granulomatous inflammation Diseases 0.000 description 1
201000011066 hemangioma Diseases 0.000 description 1
230000009033 hematopoietic malignancy Effects 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
125000004475 heteroaralkyl group Chemical group 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
229940018991 hyalgan Drugs 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
229960004171 hydroxychloroquine Drugs 0.000 description 1
230000000222 hyperoxic effect Effects 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
229960000598 infliximab Drugs 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
208000036971 interstitial lung disease 2 Diseases 0.000 description 1
201000006334 interstitial nephritis Diseases 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 1
229960001888 ipratropium Drugs 0.000 description 1
229960002198 irbesartan Drugs 0.000 description 1
YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
229960005280 isotretinoin Drugs 0.000 description 1
125000003965 isoxazolidinyl group Chemical group 0.000 description 1
201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
229940043355 kinase inhibitor Drugs 0.000 description 1
229940054136 kineret Drugs 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
210000000867 larynx Anatomy 0.000 description 1
GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 description 1
229960002367 lasofoxifene Drugs 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
210000000088 lip Anatomy 0.000 description 1
229960002394 lisinopril Drugs 0.000 description 1
RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
229960003088 loratadine Drugs 0.000 description 1
JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
229960004773 losartan Drugs 0.000 description 1
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
229960003105 metformin Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
229960002509 miconazole Drugs 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229960001664 mometasone Drugs 0.000 description 1
QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
206010028417 myasthenia gravis Diseases 0.000 description 1
208000027531 mycobacterial infectious disease Diseases 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000001491 myopia Diseases 0.000 description 1
230000004379 myopia Effects 0.000 description 1
WUDSDTPILDNBKU-UHFFFAOYSA-N n-[[4-[5-(1,3,5,8-tetraoxo-2,4,7-triazaspiro[5.5]undecan-7-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCCC2=O)C=N1 WUDSDTPILDNBKU-UHFFFAOYSA-N 0.000 description 1
KKOPLWNEKWCQGN-UHFFFAOYSA-N n-[[4-[5-(2,4,6,8,10-pentaoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)C(=O)NC2=O)C=N1 KKOPLWNEKWCQGN-UHFFFAOYSA-N 0.000 description 1
OHEXZPKETHQPRY-UHFFFAOYSA-N n-[[4-[5-(2,4,6,8,10-pentaoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]azetidine-1-carboxamide Chemical compound C1CCN1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)NC(=O)C11C(=O)NC(=O)NC1=O OHEXZPKETHQPRY-UHFFFAOYSA-N 0.000 description 1
JMGBCUNFTSUTRH-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CNC2=O)C=N1 JMGBCUNFTSUTRH-UHFFFAOYSA-N 0.000 description 1
GPXYISGDCDEYSG-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,3,7,9-tetrazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]azetidine-1-carboxamide Chemical compound C1CCN1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)NCC11C(=O)NC(=O)NC1=O GPXYISGDCDEYSG-UHFFFAOYSA-N 0.000 description 1
ZPXKNSJQYXAHJU-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 ZPXKNSJQYXAHJU-UHFFFAOYSA-N 0.000 description 1
FGZVGHWELOQBDD-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]azetidine-1-carboxamide Chemical compound C1CCN1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)CCC11C(=O)NC(=O)NC1=O FGZVGHWELOQBDD-UHFFFAOYSA-N 0.000 description 1
YHGMMVRFAGFQBB-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]propanamide Chemical compound C1=CC(CNC(=O)CC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 YHGMMVRFAGFQBB-UHFFFAOYSA-N 0.000 description 1
ZRCOOAQEMFBECJ-UHFFFAOYSA-N n-[[4-[5-(2,7,9,11-tetraoxo-1,3,8,10-tetrazaspiro[5.5]undecan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCNC2=O)C=N1 ZRCOOAQEMFBECJ-UHFFFAOYSA-N 0.000 description 1
TWSXJXUAGFEGOK-UHFFFAOYSA-N n-[[4-[5-(2,7,9,11-tetraoxo-1,3,8,10-tetrazaspiro[5.5]undecan-1-yl)pyridin-2-yl]oxyphenyl]methyl]azetidine-1-carboxamide Chemical compound C1CCN1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)NCCC11C(=O)NC(=O)NC1=O TWSXJXUAGFEGOK-UHFFFAOYSA-N 0.000 description 1
IIHIGMLODJGADR-UHFFFAOYSA-N n-[[4-[5-(6,8,10-trioxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2)C=N1 IIHIGMLODJGADR-UHFFFAOYSA-N 0.000 description 1
UMMHVDQAOBYGOM-UHFFFAOYSA-N n-[[4-[5-(6,8,10-trioxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]azetidine-1-carboxamide Chemical compound C1CCN1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1CCCC11C(=O)NC(=O)NC1=O UMMHVDQAOBYGOM-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000013642 negative control Substances 0.000 description 1
201000003142 neovascular glaucoma Diseases 0.000 description 1
208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000001777 nootropic effect Effects 0.000 description 1
201000008106 ocular cancer Diseases 0.000 description 1
239000002674 ointment Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
230000036407 pain Effects 0.000 description 1
239000003973 paint Substances 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
229960004851 pergolide Drugs 0.000 description 1
208000028169 periodontal disease Diseases 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
239000003757 phosphotransferase inhibitor Substances 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229960002702 piroxicam 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
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001184 polypeptide Chemical group 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
229960003089 pramipexole Drugs 0.000 description 1
FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
108090000765 processed proteins & peptides Chemical group 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
239000000047 product Substances 0.000 description 1
230000006785 proliferative vitreoretinopathy Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
239000003380 propellant Substances 0.000 description 1
229960002934 propentofylline Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
201000001474 proteinuria Diseases 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000005855 radiation Effects 0.000 description 1
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 1
229960000245 rasagiline Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000033458 reproduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 1
229960001879 ropinirole Drugs 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
229960002052 salbutamol Drugs 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229960004017 salmeterol Drugs 0.000 description 1
201000000306 sarcoidosis Diseases 0.000 description 1
230000037390 scarring Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
229960003946 selegiline Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
201000001223 septic arthritis Diseases 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
229960002073 sertraline Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000035939 shock Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
229960002930 sirolimus Drugs 0.000 description 1
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
230000009759 skin aging Effects 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
229960000894 sulindac Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
229940064707 sympathomimetics Drugs 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940036220 synvisc Drugs 0.000 description 1
238000012385 systemic delivery Methods 0.000 description 1
229960001685 tacrine Drugs 0.000 description 1
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960001693 terazosin Drugs 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000001467 thiazolidinediones Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000005503 thioxanyl group Chemical group 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
238000003354 tissue distribution assay Methods 0.000 description 1
230000007838 tissue remodeling Effects 0.000 description 1
230000008427 tissue turnover Effects 0.000 description 1
MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
229960004603 tolcapone 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
210000002105 tongue Anatomy 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
229960001727 tretinoin Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
230000007306 turnover Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
229940061637 xopenex Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229960004764 zafirlukast Drugs 0.000 description 1
MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
229960005332 zileuton Drugs 0.000 description 1
229940072251 zithromax Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
- 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- A61P25/22—Anxiolytics
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P3/08—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Rheumatology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Gynecology & Obstetrics (AREA)
Diabetes (AREA)
Virology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pregnancy & Childbirth (AREA)
Tropical Medicine & Parasitology (AREA)
Ophthalmology & Optometry (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Psychiatry (AREA)

CA002425283A 2000-10-26 2001-10-23 Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors Abandoned CA2425283A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US24338900P	2000-10-26	2000-10-26
US60/243,389		2000-10-26
PCT/IB2001/001986 WO2002034753A2 (en)	2000-10-26	2001-10-23	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors

Publications (1)

Publication Number	Publication Date
CA2425283A1 true CA2425283A1 (en)	2002-05-02

Family

ID=22918584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002425283A Abandoned CA2425283A1 (en)	2000-10-26	2001-10-23	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors

Country Status (32)

Country	Link
EP (1)	EP1332146A2 (cs)
JP (1)	JP2004518635A (cs)
KR (1)	KR20040004412A (cs)
CN (1)	CN1501937A (cs)
AP (1)	AP2001002318A0 (cs)
AR (1)	AR035069A1 (cs)
AU (1)	AU2002210813A1 (cs)
BG (1)	BG107653A (cs)
BR (1)	BR0114913A (cs)
CA (1)	CA2425283A1 (cs)
CZ (1)	CZ20031083A3 (cs)
EA (1)	EA005762B1 (cs)
EC (1)	ECSP034567A (cs)
EE (1)	EE200300196A (cs)
GT (1)	GT200100213A (cs)
HN (1)	HN2001000244A (cs)
HR (1)	HRP20030332A2 (cs)
HU (1)	HUP0301577A3 (cs)
IL (1)	IL154948A0 (cs)
IS (1)	IS6762A (cs)
MA (1)	MA26957A1 (cs)
MX (1)	MXPA03003735A (cs)
NO (1)	NO20031853L (cs)
OA (1)	OA12529A (cs)
PA (1)	PA8531401A1 (cs)
PE (1)	PE20020589A1 (cs)
PL (1)	PL366201A1 (cs)
SK (1)	SK4972003A3 (cs)
SV (1)	SV2003000705A (cs)
TN (1)	TNSN01149A1 (cs)
WO (1)	WO2002034753A2 (cs)
ZA (1)	ZA200302190B (cs)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MXPA03005870A (es)	2001-02-14	2005-02-14	Warner Lambert Co	Inhibirores de benzotiadiazina de metaloproteinasas de la matriz.
DOP2002000332A (es)	2001-02-14	2002-08-30	Warner Lambert Co	Inhibidores de piridina de metaloproteinasas de la matriz
JP2004518723A (ja)	2001-02-14	2004-06-24	ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー	ピリミジンマトリックスメタロプロテイナーゼ阻害剤
DOP2002000333A (es)	2001-02-14	2002-09-30	Warner Lambert Co	Derivados de acido isoftalico como inhibidores de metaloproteinasas de la matriz
PA8539501A1 (es)	2001-02-14	2002-09-30	Warner Lambert Co	Compuestos triazolo como inhibidores de mmp
US6924276B2 (en)	2001-09-10	2005-08-02	Warner-Lambert Company	Diacid-substituted heteroaryl derivatives as matrix metalloproteinase inhibitors
US6962922B2 (en)	2001-10-12	2005-11-08	Warner-Lambert Company Llc	Alkynylated quinazoline compounds
MXPA04002537A (es)	2001-10-12	2004-05-31	Warner Lambert Co	Alquinos como inhibidores de metaloproteinasa de matriz.
US6894057B2 (en)	2002-03-08	2005-05-17	Warner-Lambert Company	Oxo-azabicyclic compounds
AU2003228701A1 (en) *	2002-04-25	2003-11-10	Bristol-Myers Squibb Company	Spirobarbituric acid derivatives useful as inhibitors of matrix metalloproteases
AU2003216660A1 (en) *	2002-04-26	2003-11-10	Pfizer Products Inc.	N-substituted-heteroaryloxy-aryl-spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
JP2005527598A (ja) *	2002-04-26	2005-09-15	ファイザー・プロダクツ・インク	トリアリール−オキシ−アリール−スピロ−ピリミジン−２，４，６−トリオンメタロプロテイナーゼ阻害剤
WO2004014375A2 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Fused bicyclic metalloproteinase inhibitors
AU2003253186A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors
AU2003250470A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Pyrimidinone fused bicyclic metalloproteinase inhibitors
PA8578101A1 (es)	2002-08-13	2004-05-07	Warner Lambert Co	Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz
WO2004014378A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	3-isoquinolinone derivatives as matrix metalloproteinase inhiitors
AU2003249477A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Heterobicylcic metalloproteinase inhibitors
CA2497658A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Chromone derivatives as matrix metalloproteinase inhibitors
MXPA05001786A (es)	2002-08-13	2005-04-25	Warner Lambert Co	Derivados de azaisoquinolina como inhibidores de la metaloproteinasa de matriz.
MXPA05001603A (es) *	2002-08-13	2005-04-25	Warner Lambert Co	Derivados monociclicos como inhibidores de metaloproteinasa de matriz.
MXPA05001783A (es)	2002-08-13	2005-04-25	Warner Lambert Co	Derivados de pirimidina-2,4-diona como inhibidores de las metaloproteinasas de matriz.
US7208490B2 (en)	2002-10-07	2007-04-24	Pharmacia & Upjohn Company Llc	Tricyclic tetrahydroquinoline antibacterial agents
GB0223249D0 (en) *	2002-10-08	2002-11-13	Amersham Plc	Improved imaging agents
WO2004084903A1 (en) *	2003-03-27	2004-10-07	F. Hoffmann-La Roche Ag	Use of a trioxopyrimidine for the treatment and prevention of ocular pathologic angiogenesis
WO2004084902A1 (en) *	2003-03-28	2004-10-07	F. Hoffmann-La Roche Ag	Use of a trioxopyrimidine for the treatment of chronic wounds
FR2858232B1 (fr) *	2003-07-29	2006-03-03	Pierre Potier	Utilisation d'un derive de biguanide pour proteger la peau des radiations uvb
WO2005097133A1 (en) *	2004-04-01	2005-10-20	F. Hoffmann-La Roche Ag	Use of a trioxopyrimidine for the treatment and prevention of bronchial inflammatory diseases
DOP2006000268A (es)	2005-12-22	2007-07-31	Pfizer Prod Inc	Agentes antibacterianos
US8153166B2 (en) *	2006-06-08	2012-04-10	Chih-Hsiung Lin	Composition for prophylaxis or treatment of urinary system infection and method thereof
CN102285934B (zh) *	2009-01-08	2013-08-14	四川大学	螺环二烯酮衍生物及其制备方法和用途
MY178583A (en) *	2012-12-10	2020-10-16	Chugai Pharmaceutical Co Ltd	Hydantoin derivative
KR101594506B1 (ko) *	2014-03-20	2016-02-17	한국화학연구원	골 관련 질환 치료용 조성물
MX371090B (es)	2014-06-09	2020-01-16	Chugai Pharmaceutical Co Ltd	Composicion farmaceutica que contiene derivado de hidantoina.
AU2019387367A1 (en)	2018-11-30	2021-06-10	Nuvation Bio Inc.	Diarylhydantoin compounds and methods of use thereof
CN110092790B (zh) *	2019-06-11	2020-07-24	东北农业大学	一种生物碱类化合物及其制备方法和应用
TW202606695A (zh) *	2024-04-24	2026-02-16	美商塞普特納公司	含有取代或修飾的二胺基亞甲基嘧啶—２，４，６—三酮的副甲狀腺素１受體和腸促胰島素受體的激動劑
WO2025226892A1 (en) *	2024-04-24	2025-10-30	Septerna, Inc.	Spirocycle-containing diaminomethylene pyrimidine-2,4,6-trione agonists of parathyroid hormone 1 and incretin receptors
WO2026107328A1 (en) *	2024-11-15	2026-05-21	Septerna, Inc.	Agonists of parathyroid hormone 1 and incretin receptors
CN121648128B (zh) *	2026-02-03	2026-06-30	华中科技大学同济医学院附属同济医院	特拉唑嗪或其药学上可接受的盐在制备用于预防和/或治疗肝纤维化的药物中的应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3714093A (en) *	1970-05-19	1973-01-30	American Home Prod	Spiro [heterocycloalkyl-2'(1'h)-quinazoline]-4'(3'h)-ones
EP0989982B1 (en) *	1997-06-21	2005-08-17	Roche Diagnostics GmbH	Barbituric acid derivatives with antimetastatic and antitumor activity
US6265578B1 (en) *	1999-02-12	2001-07-24	Hoffmann-La Roche Inc.	Pyrimidine-2,4,6-triones
HN2000000137A (es) *	1999-08-12	2001-02-02	Pfizer Prod Inc	Pirimidina-2,4,6-trionas inhibidores de metaloproteinasas

2001
- 2001-10-23 CZ CZ20031083A patent/CZ20031083A3/cs unknown
- 2001-10-23 PL PL01366201A patent/PL366201A1/xx not_active Application Discontinuation
- 2001-10-23 BR BR0114913-0A patent/BR0114913A/pt not_active IP Right Cessation
- 2001-10-23 HU HU0301577A patent/HUP0301577A3/hu unknown
- 2001-10-23 IL IL15494801A patent/IL154948A0/xx unknown
- 2001-10-23 AP APAP/P/2001/002318A patent/AP2001002318A0/en unknown
- 2001-10-23 KR KR10-2003-7005753A patent/KR20040004412A/ko not_active Ceased
- 2001-10-23 AU AU2002210813A patent/AU2002210813A1/en not_active Abandoned
- 2001-10-23 EE EEP200300196A patent/EE200300196A/xx unknown
- 2001-10-23 HR HR20030332A patent/HRP20030332A2/hr not_active Application Discontinuation
- 2001-10-23 SK SK497-2003A patent/SK4972003A3/sk unknown
- 2001-10-23 CA CA002425283A patent/CA2425283A1/en not_active Abandoned
- 2001-10-23 EP EP01978721A patent/EP1332146A2/en not_active Withdrawn
- 2001-10-23 CN CNA018179231A patent/CN1501937A/zh active Pending
- 2001-10-23 EA EA200300306A patent/EA005762B1/ru not_active IP Right Cessation
- 2001-10-23 JP JP2002537743A patent/JP2004518635A/ja not_active Withdrawn
- 2001-10-23 MX MXPA03003735A patent/MXPA03003735A/es unknown
- 2001-10-23 WO PCT/IB2001/001986 patent/WO2002034753A2/en not_active Ceased
- 2001-10-23 OA OA1200300123A patent/OA12529A/en unknown
- 2001-10-24 HN HN2001000244A patent/HN2001000244A/es unknown
- 2001-10-24 AR ARP010104977A patent/AR035069A1/es unknown
- 2001-10-25 SV SV2001000705A patent/SV2003000705A/es unknown
- 2001-10-25 PE PE2001001060A patent/PE20020589A1/es not_active Application Discontinuation
- 2001-10-25 GT GT200100213A patent/GT200100213A/es unknown
- 2001-10-25 TN TNTNSN01149A patent/TNSN01149A1/fr unknown
- 2001-10-26 PA PA20018531401A patent/PA8531401A1/es unknown
2003
- 2003-03-19 ZA ZA200302190A patent/ZA200302190B/en unknown
- 2003-03-20 BG BG107653A patent/BG107653A/bg unknown
- 2003-03-27 IS IS6762A patent/IS6762A/is unknown
- 2003-04-22 MA MA27117A patent/MA26957A1/fr unknown
- 2003-04-24 NO NO20031853A patent/NO20031853L/no not_active Application Discontinuation
- 2003-04-25 EC EC2003004567A patent/ECSP034567A/es unknown

Also Published As

Publication number	Publication date
CN1501937A (zh)	2004-06-02
NO20031853L (no)	2003-06-23
PL366201A1 (en)	2005-01-24
MXPA03003735A (es)	2003-07-28
AP2001002318A0 (en)	2001-12-31
SV2003000705A (es)	2003-01-13
TNSN01149A1 (fr)	2005-11-10
ZA200302190B (en)	2004-04-28
GT200100213A (es)	2002-07-03
KR20040004412A (ko)	2004-01-13
IS6762A (is)	2003-03-27
BG107653A (bg)	2003-12-31
HN2001000244A (es)	2003-11-07
JP2004518635A (ja)	2004-06-24
SK4972003A3 (en)	2004-05-04
EP1332146A2 (en)	2003-08-06
WO2002034753A2 (en)	2002-05-02
IL154948A0 (en)	2003-10-31
HUP0301577A3 (en)	2006-02-28
HRP20030332A2 (en)	2003-06-30
WO2002034753A3 (en)	2002-08-15
EE200300196A (et)	2003-10-15
AU2002210813A1 (en)	2002-05-06
MA26957A1 (fr)	2004-12-20
PE20020589A1 (es)	2002-07-06
ECSP034567A (es)	2003-06-25
NO20031853D0 (no)	2003-04-24
HUP0301577A2 (hu)	2003-11-28
OA12529A (en)	2006-06-02
EA005762B1 (ru)	2005-06-30
AR035069A1 (es)	2004-04-14
PA8531401A1 (es)	2003-06-30
EA200300306A1 (ru)	2003-08-28
BR0114913A (pt)	2003-07-01
CZ20031083A3 (cs)	2004-03-17

Legal Events

Date	Code	Title	Description
2003-04-08	EEER	Examination request
2007-10-23	FZDE	Discontinued

Publication	Publication Date	Title
US6841671B2 (en)	2005-01-11	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501833B1 (en)	2005-11-02	N-substituted-heteroaryloxy-aryl-spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
US6919332B2 (en)	2005-07-19	N-substituted-heteroaryloxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1332146A2 (en)	2003-08-06	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501834B1 (en)	2005-09-07	Triaryl-oxy-aryl-spiro-pyrimidine-2, 4, 6-trione metalloproteinase inhibitors
US6706723B2 (en)	2004-03-16	Pyrimidine-2,4,6-trione metalloproteinase inhibitors
US20040039012A1 (en)	2004-02-26	Pyridine fused bicyclic metalloproteinase inhibitors
EP1501515B1 (en)	2005-11-02	Triaryl-oxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors