AU2008286946B2 - Heteroaryl amide analogues - Google Patents
Heteroaryl amide analogues Download PDFInfo
- Publication number
- AU2008286946B2 AU2008286946B2 AU2008286946A AU2008286946A AU2008286946B2 AU 2008286946 B2 AU2008286946 B2 AU 2008286946B2 AU 2008286946 A AU2008286946 A AU 2008286946A AU 2008286946 A AU2008286946 A AU 2008286946A AU 2008286946 B2 AU2008286946 B2 AU 2008286946B2
- Authority
- AU
- Australia
- Prior art keywords
- indole
- pyrimidin
- carboxamide
- methyl
- chloro
- Prior art date
- 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.)
- Ceased
Links
- -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 128
- 150000001875 compounds Chemical class 0.000 claims abstract description 218
- 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 124
- 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 123
- 208000002193 Pain Diseases 0.000 claims abstract description 105
- 230000036407 pain Effects 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 206010061218 Inflammation Diseases 0.000 claims abstract description 18
- 230000004054 inflammatory process Effects 0.000 claims abstract description 18
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 208000022873 Ocular disease Diseases 0.000 claims abstract description 6
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
- 208000026278 immune system disease Diseases 0.000 claims abstract description 4
- 230000000926 neurological effect Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims description 65
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 208000004296 neuralgia Diseases 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 150000005215 alkyl ethers Chemical class 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 17
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 206010016654 Fibrosis Diseases 0.000 claims description 13
- 208000006673 asthma Diseases 0.000 claims description 13
- 208000021722 neuropathic pain Diseases 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 13
- 206010029240 Neuritis Diseases 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 230000001154 acute effect Effects 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 210000005036 nerve Anatomy 0.000 claims description 8
- 201000008482 osteoarthritis Diseases 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- VVFCLFKBZYOEQN-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N)=CN1C1=NC=CC=N1 VVFCLFKBZYOEQN-UHFFFAOYSA-N 0.000 claims description 6
- 208000008035 Back Pain Diseases 0.000 claims description 6
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 206010025135 lupus erythematosus Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 230000009529 traumatic brain injury Effects 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 5
- 201000005569 Gout Diseases 0.000 claims description 5
- 206010023230 Joint stiffness Diseases 0.000 claims description 5
- 206010039710 Scleroderma Diseases 0.000 claims description 5
- 206010003246 arthritis Diseases 0.000 claims description 5
- 230000007882 cirrhosis Effects 0.000 claims description 5
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 206010019233 Headaches Diseases 0.000 claims description 4
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 230000008653 root damage Effects 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- CQZYCDBHEULOFD-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=N1 CQZYCDBHEULOFD-UHFFFAOYSA-N 0.000 claims description 3
- ATWCIOGPHPGOGT-UHFFFAOYSA-N 2-(1-adamantyl)-n-(4-chloro-1-pyrimidin-2-ylindol-3-yl)acetamide Chemical compound C1=C(NC(=O)CC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 ATWCIOGPHPGOGT-UHFFFAOYSA-N 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 206010068065 Burning mouth syndrome Diseases 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
- 208000001387 Causalgia Diseases 0.000 claims description 3
- 206010014020 Ear pain Diseases 0.000 claims description 3
- 206010015958 Eye pain Diseases 0.000 claims description 3
- 206010016059 Facial pain Diseases 0.000 claims description 3
- 208000033830 Hot Flashes Diseases 0.000 claims description 3
- 206010060800 Hot flush Diseases 0.000 claims description 3
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
- 208000000112 Myalgia Diseases 0.000 claims description 3
- 206010049002 Scar pain Diseases 0.000 claims description 3
- 206010042496 Sunburn Diseases 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 3
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 3
- 208000004967 femoral neuropathy Diseases 0.000 claims description 3
- 208000032184 meralgia paresthetica Diseases 0.000 claims description 3
- 208000013465 muscle pain Diseases 0.000 claims description 3
- JZYSYXDHRXPHKQ-UHFFFAOYSA-N n-(1-adamantylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 JZYSYXDHRXPHKQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000008764 nerve damage Effects 0.000 claims description 3
- 201000009985 neuronitis Diseases 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000002435 venom Substances 0.000 claims description 3
- 210000001048 venom Anatomy 0.000 claims description 3
- 231100000611 venom Toxicity 0.000 claims description 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- GGNNKOPRPONVQA-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3,4-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2C(C(=O)O)=CN1C1=NC=CC=N1 GGNNKOPRPONVQA-UHFFFAOYSA-N 0.000 claims description 2
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 2
- ANAIABPQJGVDQA-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 ANAIABPQJGVDQA-UHFFFAOYSA-N 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- 206010072005 Spinal pain Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- YJCCGSIXSDHVLI-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YJCCGSIXSDHVLI-UHFFFAOYSA-N 0.000 claims description 2
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 2
- STWNGMSGPBZFMX-UHFFFAOYSA-N pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC(=O)C1=CC=CN=C1 STWNGMSGPBZFMX-UHFFFAOYSA-N 0.000 claims description 2
- LKMRWAUYFFIPLS-UHFFFAOYSA-N 1-(3-cyanopyridin-2-yl)-4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)indole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 LKMRWAUYFFIPLS-UHFFFAOYSA-N 0.000 claims 1
- JCSUYDVTWQJBCI-UHFFFAOYSA-N 1-(3-ethylpyrazin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound CCC1=NC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 JCSUYDVTWQJBCI-UHFFFAOYSA-N 0.000 claims 1
- DVQJAIGHURJMKU-UHFFFAOYSA-N 1-(5-fluoropyrimidin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound N1=CC(F)=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 DVQJAIGHURJMKU-UHFFFAOYSA-N 0.000 claims 1
- FLPKUPFRCHXLDY-UHFFFAOYSA-N 1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FLPKUPFRCHXLDY-UHFFFAOYSA-N 0.000 claims 1
- STSVLKXCUGQLSX-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C2=CC=CC=C2C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 STSVLKXCUGQLSX-UHFFFAOYSA-N 0.000 claims 1
- RVHSUIQQODJJDG-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]pentanoic acid Chemical compound C12=CC=CC=C2N(C(C(O)=O)CCC)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 RVHSUIQQODJJDG-UHFFFAOYSA-N 0.000 claims 1
- QYDVTNYUERGOIZ-UHFFFAOYSA-N 3-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCOCC1 QYDVTNYUERGOIZ-UHFFFAOYSA-N 0.000 claims 1
- GHPANTLFSOVSKV-UHFFFAOYSA-N 4-bromo-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Br)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 GHPANTLFSOVSKV-UHFFFAOYSA-N 0.000 claims 1
- SZMUXKSFYOVBLZ-UHFFFAOYSA-N 4-chloro-1-[2-(dimethylamino)ethyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 SZMUXKSFYOVBLZ-UHFFFAOYSA-N 0.000 claims 1
- KCGVNAOUYOFNIB-UHFFFAOYSA-N 4-chloro-1-[3-(dimethylamino)propyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 KCGVNAOUYOFNIB-UHFFFAOYSA-N 0.000 claims 1
- FTKQORPRCLRPNX-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-(3,3,5-trimethylcyclohexyl)indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FTKQORPRCLRPNX-UHFFFAOYSA-N 0.000 claims 1
- XUTHDCGXPKNBGI-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XUTHDCGXPKNBGI-UHFFFAOYSA-N 0.000 claims 1
- GBQVSGPQEXAYLT-VMBOVVBDSA-N 4-chloro-N-[[(1R)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C([C@]1(C2(C)C)[H])C2CCC1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 GBQVSGPQEXAYLT-VMBOVVBDSA-N 0.000 claims 1
- LRSPAPPWXYSXKT-UHFFFAOYSA-N 4-chloro-n-(2,3-diphenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1=CC=CC=C1 LRSPAPPWXYSXKT-UHFFFAOYSA-N 0.000 claims 1
- WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
- YTJSTQCNEZOXLZ-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 YTJSTQCNEZOXLZ-UHFFFAOYSA-N 0.000 claims 1
- QKSVJBHORLUNPE-UHFFFAOYSA-N 4-chloro-n-(2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 QKSVJBHORLUNPE-UHFFFAOYSA-N 0.000 claims 1
- RGVNVQZTKWHPNU-UHFFFAOYSA-N 4-chloro-n-(3-cyclopentyl-2-phenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1CCCC1 RGVNVQZTKWHPNU-UHFFFAOYSA-N 0.000 claims 1
- NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
- JNXFOEOZSYOZCN-UHFFFAOYSA-N 4-chloro-n-(3-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CCNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JNXFOEOZSYOZCN-UHFFFAOYSA-N 0.000 claims 1
- OYPGSBLIRKBVFP-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OYPGSBLIRKBVFP-UHFFFAOYSA-N 0.000 claims 1
- KQVGATDURWAKBQ-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 KQVGATDURWAKBQ-UHFFFAOYSA-N 0.000 claims 1
- YPHBXMYPYMXXKK-UHFFFAOYSA-N 4-chloro-n-(4-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCCCC1=CC=CC=C1 YPHBXMYPYMXXKK-UHFFFAOYSA-N 0.000 claims 1
- QNCAVWZEJVXGSL-UHFFFAOYSA-N 4-chloro-n-(cycloheptylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1CCCCCC1 QNCAVWZEJVXGSL-UHFFFAOYSA-N 0.000 claims 1
- IXEUUUTXRDEESS-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycycloheptyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCCC1 IXEUUUTXRDEESS-UHFFFAOYSA-N 0.000 claims 1
- QHXNCWYVURIMHA-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 QHXNCWYVURIMHA-UHFFFAOYSA-N 0.000 claims 1
- MJSYWSCNWAHYJT-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclopentyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCC1 MJSYWSCNWAHYJT-UHFFFAOYSA-N 0.000 claims 1
- NDLYAXIBRQFGQO-UHFFFAOYSA-N 4-chloro-n-[(4-hydroxythian-4-yl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCSCC1 NDLYAXIBRQFGQO-UHFFFAOYSA-N 0.000 claims 1
- HUMJOZFHUVTLGE-UHFFFAOYSA-N 4-chloro-n-[2-(2,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound FC1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 HUMJOZFHUVTLGE-UHFFFAOYSA-N 0.000 claims 1
- TZKDHXJYDQGLFK-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 TZKDHXJYDQGLFK-UHFFFAOYSA-N 0.000 claims 1
- WSZARDIHNUIOKO-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 WSZARDIHNUIOKO-UHFFFAOYSA-N 0.000 claims 1
- ZHQIUAHDKPUOKT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 ZHQIUAHDKPUOKT-UHFFFAOYSA-N 0.000 claims 1
- XKBDSAHQQPZOGB-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 XKBDSAHQQPZOGB-UHFFFAOYSA-N 0.000 claims 1
- VZMLUTLVCOGUEI-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperazin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCNCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 VZMLUTLVCOGUEI-UHFFFAOYSA-N 0.000 claims 1
- JFUGGKDZPSAIOY-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JFUGGKDZPSAIOY-UHFFFAOYSA-N 0.000 claims 1
- ADFDHZKHHVMNEO-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-[2-(dimethylamino)ethyl]indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(Cl)C=C1 ADFDHZKHHVMNEO-UHFFFAOYSA-N 0.000 claims 1
- MWHKATVDYBPMRL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(Cl)C=C1 MWHKATVDYBPMRL-UHFFFAOYSA-N 0.000 claims 1
- LYJDGLXLBJVRCJ-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 LYJDGLXLBJVRCJ-UHFFFAOYSA-N 0.000 claims 1
- FSSJSUBFNKMDTL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FSSJSUBFNKMDTL-UHFFFAOYSA-N 0.000 claims 1
- OTOKCOMTTJYKQA-UHFFFAOYSA-N 4-chloro-n-[2-(4-fluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OTOKCOMTTJYKQA-UHFFFAOYSA-N 0.000 claims 1
- YCOBLIXIJZXBLR-UHFFFAOYSA-N 4-chloro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 YCOBLIXIJZXBLR-UHFFFAOYSA-N 0.000 claims 1
- FKCPUVYYGVELQN-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FKCPUVYYGVELQN-UHFFFAOYSA-N 0.000 claims 1
- FAURIVHGMPPVLE-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FAURIVHGMPPVLE-UHFFFAOYSA-N 0.000 claims 1
- RUEJAIZHINZZDH-SUMWQHHRSA-N 4-chloro-n-[[(1s,2r)-2-hydroxycyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound O[C@@H]1CCCC[C@H]1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 RUEJAIZHINZZDH-SUMWQHHRSA-N 0.000 claims 1
- KAENIFYSTKFXFA-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclobutyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCC1 KAENIFYSTKFXFA-UHFFFAOYSA-N 0.000 claims 1
- OXHUCARSSRATMO-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 OXHUCARSSRATMO-UHFFFAOYSA-N 0.000 claims 1
- DERUNCJUFQBRRW-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 DERUNCJUFQBRRW-UHFFFAOYSA-N 0.000 claims 1
- GDLABCVOIPYOGZ-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methylpiperazin-1-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1CN(C)CCN1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GDLABCVOIPYOGZ-UHFFFAOYSA-N 0.000 claims 1
- PIODEHXTCAOMMR-UHFFFAOYSA-N 4-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCOCC1 PIODEHXTCAOMMR-UHFFFAOYSA-N 0.000 claims 1
- PDAPGQZQFOLEID-UHFFFAOYSA-N 4-cyano-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(C#N)=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 PDAPGQZQFOLEID-UHFFFAOYSA-N 0.000 claims 1
- AHBGYVPATHFLKO-UHFFFAOYSA-N 4-fluoro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 AHBGYVPATHFLKO-UHFFFAOYSA-N 0.000 claims 1
- QBYJBBMCFSHBTP-UHFFFAOYSA-N 4-fluoro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 QBYJBBMCFSHBTP-UHFFFAOYSA-N 0.000 claims 1
- GEJZOVZEMUQBQK-UHFFFAOYSA-N 4-fluoro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 GEJZOVZEMUQBQK-UHFFFAOYSA-N 0.000 claims 1
- QJKMIQZBXGSLAK-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 QJKMIQZBXGSLAK-UHFFFAOYSA-N 0.000 claims 1
- GUCURJGUSGPXIC-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GUCURJGUSGPXIC-UHFFFAOYSA-N 0.000 claims 1
- SCBJKZLZBBFRSW-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 SCBJKZLZBBFRSW-UHFFFAOYSA-N 0.000 claims 1
- JVYOELCASNKUKK-UHFFFAOYSA-N 4-methyl-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 JVYOELCASNKUKK-UHFFFAOYSA-N 0.000 claims 1
- OIKQYDBRBPIGDB-UHFFFAOYSA-N 4-methyl-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 OIKQYDBRBPIGDB-UHFFFAOYSA-N 0.000 claims 1
- GPRICYCQYFLCSD-UHFFFAOYSA-N 7-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=CN1C1=NC=CC=N1 GPRICYCQYFLCSD-UHFFFAOYSA-N 0.000 claims 1
- UUCNBNVIKYMGID-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[2-(dimethylamino)ethyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 UUCNBNVIKYMGID-UHFFFAOYSA-N 0.000 claims 1
- PFXSYZMQBXGURF-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 PFXSYZMQBXGURF-UHFFFAOYSA-N 0.000 claims 1
- AFWMMWSWXVYLDZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 AFWMMWSWXVYLDZ-UHFFFAOYSA-N 0.000 claims 1
- NCRXZRNQZWAQQE-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(C)=CC=CC=2N1C1=NC=CC=N1 NCRXZRNQZWAQQE-UHFFFAOYSA-N 0.000 claims 1
- GXQNBGUOACJYPR-UHFFFAOYSA-N n-(2-adamantyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NC2C3CC4CC(C3)CC2C4)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 GXQNBGUOACJYPR-UHFFFAOYSA-N 0.000 claims 1
- TZMRUUUUXCOCJO-UHFFFAOYSA-N n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 TZMRUUUUXCOCJO-UHFFFAOYSA-N 0.000 claims 1
- VHQQVRXPSSCPOI-UHFFFAOYSA-N n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 VHQQVRXPSSCPOI-UHFFFAOYSA-N 0.000 claims 1
- KAKVGAOZPOYJDQ-UHFFFAOYSA-N n-[(1-morpholin-4-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(N2CCOCC2)CCCCC1 KAKVGAOZPOYJDQ-UHFFFAOYSA-N 0.000 claims 1
- YYRCJXPQPPOVIB-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YYRCJXPQPPOVIB-UHFFFAOYSA-N 0.000 claims 1
- HCSZLWUZTCBTMA-UHFFFAOYSA-N n-[2-(1-adamantyl)-2-hydroxyethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(O)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 HCSZLWUZTCBTMA-UHFFFAOYSA-N 0.000 claims 1
- MUCNGXXFDVORKK-UHFFFAOYSA-N n-[2-(1-adamantyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 MUCNGXXFDVORKK-UHFFFAOYSA-N 0.000 claims 1
- CSLSUGNOOSSJQR-UHFFFAOYSA-N n-[2-(2-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=CC=C1Br CSLSUGNOOSSJQR-UHFFFAOYSA-N 0.000 claims 1
- QCWQBVHZWNBJBZ-UHFFFAOYSA-N n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=C(F)C(F)=CC=1)N1CCCCC1 QCWQBVHZWNBJBZ-UHFFFAOYSA-N 0.000 claims 1
- PSJGDAHXFKXRLX-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=C(Br)C=C1 PSJGDAHXFKXRLX-UHFFFAOYSA-N 0.000 claims 1
- JUPFTIKYNNMMRM-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 JUPFTIKYNNMMRM-UHFFFAOYSA-N 0.000 claims 1
- XABGESGCAUJZCE-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 XABGESGCAUJZCE-UHFFFAOYSA-N 0.000 claims 1
- MSFLUMKJDNRDIJ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-4-methyl-1-pyrazin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=NC=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 MSFLUMKJDNRDIJ-UHFFFAOYSA-N 0.000 claims 1
- VZUNDRBCOUPZBZ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 VZUNDRBCOUPZBZ-UHFFFAOYSA-N 0.000 claims 1
- XDOZISHMSFCTLB-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-(3-cyanopyridin-2-yl)-4-methylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 XDOZISHMSFCTLB-UHFFFAOYSA-N 0.000 claims 1
- XVBJHQNEIHWFGJ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 XVBJHQNEIHWFGJ-UHFFFAOYSA-N 0.000 claims 1
- NMZOKSLIMKWCSU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 NMZOKSLIMKWCSU-UHFFFAOYSA-N 0.000 claims 1
- VPWBKIPGUKDQEG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrazin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=NC=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 VPWBKIPGUKDQEG-UHFFFAOYSA-N 0.000 claims 1
- GCXBEEBQOLYVLA-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 GCXBEEBQOLYVLA-UHFFFAOYSA-N 0.000 claims 1
- QPMCJYOLEYBWBR-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-methylpentyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 QPMCJYOLEYBWBR-UHFFFAOYSA-N 0.000 claims 1
- MNQGSJTUNWNUSP-UHFFFAOYSA-N n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 MNQGSJTUNWNUSP-UHFFFAOYSA-N 0.000 claims 1
- OGULYLDMHWGPIK-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(F)=CC=1)N1CCCCC1 OGULYLDMHWGPIK-UHFFFAOYSA-N 0.000 claims 1
- BSKWQGRALUGAQK-UHFFFAOYSA-N n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 BSKWQGRALUGAQK-UHFFFAOYSA-N 0.000 claims 1
- NYPBTJPAMLSQOQ-UHFFFAOYSA-N n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 NYPBTJPAMLSQOQ-UHFFFAOYSA-N 0.000 claims 1
- KKGOARLCUKPGGM-UHFFFAOYSA-N n-[[1-(4-chloro-3-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C2(CNC(=O)C=3C4=CC=CC=C4N(C=4N=CC=CN=4)C=3)CCCCC2)=C1 KKGOARLCUKPGGM-UHFFFAOYSA-N 0.000 claims 1
- RFBYRXHGAHIWMU-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 RFBYRXHGAHIWMU-UHFFFAOYSA-N 0.000 claims 1
- OXYXAQHHQONHMX-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 OXYXAQHHQONHMX-UHFFFAOYSA-N 0.000 claims 1
- KYMISPJLBMCXEX-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 KYMISPJLBMCXEX-UHFFFAOYSA-N 0.000 claims 1
- FTRLLIYBIMGYRE-UHFFFAOYSA-N n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FTRLLIYBIMGYRE-UHFFFAOYSA-N 0.000 claims 1
- ITLQNYHTRGSTRM-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(C)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 ITLQNYHTRGSTRM-UHFFFAOYSA-N 0.000 claims 1
- RVVOKOYZHSYRLP-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclopentyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCC1 RVVOKOYZHSYRLP-UHFFFAOYSA-N 0.000 claims 1
- JBBHYKYPYOHBHL-UHFFFAOYSA-N n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 JBBHYKYPYOHBHL-UHFFFAOYSA-N 0.000 claims 1
- FOZCCIXBLOUDJL-UHFFFAOYSA-N n-[[1-(6-methylpyridin-3-yl)cyclohexyl]methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1(CNC(=O)C=2C3=C(C=CC=C3N(C=3N=CC=CN=3)C=2)C(F)(F)F)CCCCC1 FOZCCIXBLOUDJL-UHFFFAOYSA-N 0.000 claims 1
- XTFXNXJNPJKQNQ-UHFFFAOYSA-N n-[[1-(6-methylpyridin-3-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XTFXNXJNPJKQNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 26
- 239000003446 ligand Substances 0.000 abstract description 10
- 102000015554 Dopamine receptor Human genes 0.000 abstract 1
- 108050004812 Dopamine receptor Proteins 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 88
- 230000000694 effects Effects 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 description 50
- 238000003556 assay Methods 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 210000004027 cell Anatomy 0.000 description 36
- 238000012360 testing method Methods 0.000 description 35
- 239000007787 solid Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 125000000623 heterocyclic group Chemical group 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- 239000004480 active ingredient Substances 0.000 description 24
- 150000003857 carboxamides Chemical class 0.000 description 23
- 238000000576 coating method Methods 0.000 description 23
- 238000009472 formulation Methods 0.000 description 23
- 239000005557 antagonist Substances 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- 229940044551 receptor antagonist Drugs 0.000 description 19
- 239000002464 receptor antagonist Substances 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 125000002252 acyl group Chemical group 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 16
- 229940079593 drug Drugs 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000005236 alkanoylamino group Chemical group 0.000 description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 15
- 229940121363 anti-inflammatory agent Drugs 0.000 description 15
- 239000002260 anti-inflammatory agent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 238000013270 controlled release Methods 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- 238000001727 in vivo Methods 0.000 description 13
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 239000003981 vehicle Substances 0.000 description 13
- 239000003643 water by type Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 12
- 239000003755 preservative agent Substances 0.000 description 12
- 230000004913 activation Effects 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- 125000001188 haloalkyl group Chemical group 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 230000001404 mediated effect Effects 0.000 description 11
- 238000009739 binding Methods 0.000 description 10
- 150000004677 hydrates Chemical class 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 230000004044 response Effects 0.000 description 10
- 208000024891 symptom Diseases 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 230000004761 fibrosis Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 210000000548 hind-foot Anatomy 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 230000000699 topical effect Effects 0.000 description 8
- AINBWHVBVYQQAZ-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindole-3-carboxylic acid Chemical compound C12=CC=CC(Cl)=C2C(C(=O)O)=CN1C1=NC=CC=N1 AINBWHVBVYQQAZ-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 239000000730 antalgic agent Substances 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000002513 implantation Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 210000004185 liver Anatomy 0.000 description 7
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000018 receptor agonist Substances 0.000 description 7
- 229940044601 receptor agonist Drugs 0.000 description 7
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 206010020751 Hypersensitivity Diseases 0.000 description 6
- 239000004909 Moisturizer Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 208000026935 allergic disease Diseases 0.000 description 6
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 230000001684 chronic effect Effects 0.000 description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 239000003974 emollient agent Substances 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 210000002216 heart Anatomy 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000002483 medication Methods 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 230000001333 moisturizer Effects 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 208000033808 peripheral neuropathy Diseases 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229940075993 receptor modulator Drugs 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 230000019491 signal transduction Effects 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 229910052722 tritium Inorganic materials 0.000 description 6
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000007995 HEPES buffer Substances 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- 239000008896 Opium Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229930006000 Sucrose Natural products 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
- 208000005298 acute pain Diseases 0.000 description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 208000010668 atopic eczema Diseases 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- 238000002648 combination therapy Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 235000013355 food flavoring agent Nutrition 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 230000009610 hypersensitivity Effects 0.000 description 5
- 238000000099 in vitro assay Methods 0.000 description 5
- 239000006210 lotion Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 201000001119 neuropathy Diseases 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229960001027 opium Drugs 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 208000000094 Chronic Pain Diseases 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
- 208000004454 Hyperalgesia Diseases 0.000 description 4
- 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 4
- 239000004166 Lanolin Substances 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 206010039897 Sedation Diseases 0.000 description 4
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-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
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 230000000172 allergic effect Effects 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 210000001124 body fluid Anatomy 0.000 description 4
- 239000010839 body fluid Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 125000004438 haloalkoxy group Chemical group 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 235000019388 lanolin Nutrition 0.000 description 4
- 229940039717 lanolin Drugs 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000004770 neurodegeneration Effects 0.000 description 4
- 230000007823 neuropathy Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 210000003994 retinal ganglion cell Anatomy 0.000 description 4
- 230000036280 sedation Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229940083542 sodium Drugs 0.000 description 4
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 239000012049 topical pharmaceutical composition Substances 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- AOWOVTUGHIKKNC-UHFFFAOYSA-N 1-(trifluoromethyl)indole Chemical compound C1=CC=C2N(C(F)(F)F)C=CC2=C1 AOWOVTUGHIKKNC-UHFFFAOYSA-N 0.000 description 3
- VUQPUDLWSOEMHW-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxylic acid Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C=C1C(O)=O VUQPUDLWSOEMHW-UHFFFAOYSA-N 0.000 description 3
- AWJJLYZBWRIBCZ-UGTJMOTHSA-N 3'-O-(4-Benzoyl)benzoyl ATP Chemical compound O([C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=2N=CN=C(C=2N=C1)N)C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 AWJJLYZBWRIBCZ-UGTJMOTHSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
- 239000001856 Ethyl cellulose Substances 0.000 description 3
- 206010018364 Glomerulonephritis Diseases 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 206010019842 Hepatomegaly Diseases 0.000 description 3
- 102000000589 Interleukin-1 Human genes 0.000 description 3
- 108010002352 Interleukin-1 Proteins 0.000 description 3
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 description 3
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 208000003251 Pruritus Diseases 0.000 description 3
- 206010063837 Reperfusion injury Diseases 0.000 description 3
- 241000283984 Rodentia Species 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008484 agonism Effects 0.000 description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
- 125000005219 aminonitrile group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000001363 autoimmune Effects 0.000 description 3
- 210000003050 axon Anatomy 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 239000002702 enteric coating Substances 0.000 description 3
- 238000009505 enteric coating Methods 0.000 description 3
- 235000019325 ethyl cellulose Nutrition 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000002458 infectious effect Effects 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- MKXZASYAUGDDCJ-CGTJXYLNSA-N levomethorphan Chemical compound C([C@H]12)CCC[C@@]11CCN(C)[C@@H]2CC2=CC=C(OC)C=C21 MKXZASYAUGDDCJ-CGTJXYLNSA-N 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 230000004807 localization Effects 0.000 description 3
- 238000013507 mapping Methods 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 230000004112 neuroprotection Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 229940127240 opiate Drugs 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 229960002085 oxycodone Drugs 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 3
- 229960000482 pethidine Drugs 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 230000020341 sensory perception of pain Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 210000001835 viscera Anatomy 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- MOZSPXWHVLPQGG-UHFFFAOYSA-N (1-pyridin-3-ylcyclohexyl)methanamine Chemical compound C=1C=CN=CC=1C1(CN)CCCCC1 MOZSPXWHVLPQGG-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- NCGQGCZGESFMTR-UHFFFAOYSA-N 1-(4-chloro-1-pyrimidin-2-ylindol-3-yl)-2,2,2-trifluoroethanone Chemical compound C12=CC=CC(Cl)=C2C(C(=O)C(F)(F)F)=CN1C1=NC=CC=N1 NCGQGCZGESFMTR-UHFFFAOYSA-N 0.000 description 2
- BJHNBWVRFDXMNQ-UHFFFAOYSA-N 1-(4-chloro-1h-indol-3-yl)-2,2,2-trifluoroethanone Chemical compound C1=CC(Cl)=C2C(C(=O)C(F)(F)F)=CNC2=C1 BJHNBWVRFDXMNQ-UHFFFAOYSA-N 0.000 description 2
- FPHOPYWEFQYZLM-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 FPHOPYWEFQYZLM-UHFFFAOYSA-N 0.000 description 2
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 2
- IEDJVYVKAFONAU-UHFFFAOYSA-N 1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carbaldehyde Chemical compound C1=C(C=O)C=2C(C(F)(F)F)=CC=CC=2N1C1=NC=CC=N1 IEDJVYVKAFONAU-UHFFFAOYSA-N 0.000 description 2
- JVYKYTXNSVXYLU-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=CN1C1=NC=CC=N1 JVYKYTXNSVXYLU-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- YGSKOERZFUTESV-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-indole-3-carbaldehyde Chemical compound FC(F)(F)C1=CC=CC2=C1C(C=O)=CN2 YGSKOERZFUTESV-UHFFFAOYSA-N 0.000 description 2
- IPAFHZDRYAWZOB-UHFFFAOYSA-N 4-bromo-1h-indole-3-carbaldehyde Chemical compound BrC1=CC=CC2=C1C(C=O)=CN2 IPAFHZDRYAWZOB-UHFFFAOYSA-N 0.000 description 2
- NQXRVSXSNKUQEH-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carbaldehyde Chemical compound C1=C(C=O)C=2C(Cl)=CC=NC=2N1C1=NC=CC=N1 NQXRVSXSNKUQEH-UHFFFAOYSA-N 0.000 description 2
- IQIRESHMJBJGHL-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxylic acid Chemical compound C12=NC=CC(Cl)=C2C(C(=O)O)=CN1C1=NC=CC=N1 IQIRESHMJBJGHL-UHFFFAOYSA-N 0.000 description 2
- DYWWVLQMUUZZRJ-UHFFFAOYSA-N 4-chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde Chemical compound ClC1=CC=NC2=C1C(C=O)=CN2 DYWWVLQMUUZZRJ-UHFFFAOYSA-N 0.000 description 2
- JIEFHTMCDUIJDU-UHFFFAOYSA-N 4-chloro-n-diazonio-1-pyrimidin-2-ylindole-3-carboximidate Chemical compound C1=C(C(=O)N=[N+]=[N-])C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 JIEFHTMCDUIJDU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 230000002407 ATP formation Effects 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 235000006491 Acacia senegal Nutrition 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 235000003911 Arachis Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 108091006146 Channels Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 206010012434 Dermatitis allergic Diseases 0.000 description 2
- 206010052804 Drug tolerance Diseases 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 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 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 208000035690 Familial cold urticaria Diseases 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 206010065390 Inflammatory pain Diseases 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000010718 Multiple Organ Failure Diseases 0.000 description 2
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 2
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 208000004550 Postoperative Pain Diseases 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- 206010040744 Sinus headache Diseases 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
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
- 108010062740 TRPV Cation Channels Proteins 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 206010046543 Urinary incontinence Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000048 adrenergic agonist Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920013820 alkyl cellulose Polymers 0.000 description 2
- 125000005011 alkyl ether group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940125684 antimigraine agent Drugs 0.000 description 2
- 239000002282 antimigraine agent Substances 0.000 description 2
- 208000007474 aortic aneurysm Diseases 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000008499 blood brain barrier function Effects 0.000 description 2
- 210000001218 blood-brain barrier Anatomy 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 2
- 229960001736 buprenorphine Drugs 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 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
- 229960000590 celecoxib Drugs 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 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 2
- 238000007405 data analysis Methods 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 230000001934 delay Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 229960002069 diamorphine Drugs 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- YBHMEJYYTNFENW-UHFFFAOYSA-N ethyl 1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC=C2N1CC1=NC=CN1C YBHMEJYYTNFENW-UHFFFAOYSA-N 0.000 description 2
- 206010064570 familial cold autoinflammatory syndrome Diseases 0.000 description 2
- 229960002428 fentanyl Drugs 0.000 description 2
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229940044170 formate Drugs 0.000 description 2
- 229960002870 gabapentin Drugs 0.000 description 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 230000026781 habituation Effects 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 description 2
- 229960001410 hydromorphone Drugs 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 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
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229960003406 levorphanol Drugs 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000002540 macrophage Anatomy 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- QXAUTQFAWKKNLM-UHFFFAOYSA-N methyl indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CNC2=C1 QXAUTQFAWKKNLM-UHFFFAOYSA-N 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- SOHCYNFHNYKSTM-UHFFFAOYSA-N methylsulfinylmethane;oxolane Chemical compound CS(C)=O.C1CCOC1 SOHCYNFHNYKSTM-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 210000000274 microglia Anatomy 0.000 description 2
- 230000003228 microsomal effect Effects 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 210000001616 monocyte Anatomy 0.000 description 2
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 206010028417 myasthenia gravis Diseases 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 description 2
- 229960000805 nalbuphine Drugs 0.000 description 2
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 2
- 229960004127 naloxone Drugs 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 201000008383 nephritis Diseases 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 210000000929 nociceptor Anatomy 0.000 description 2
- 108091008700 nociceptors Proteins 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 229960005118 oxymorphone Drugs 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229960005301 pentazocine Drugs 0.000 description 2
- 210000000578 peripheral nerve Anatomy 0.000 description 2
- 210000001428 peripheral nervous system Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 108090000765 processed proteins & peptides Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 230000002207 retinal effect Effects 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
- 229960000371 rofecoxib Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 2
- 229960002218 sodium chlorite Drugs 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical group C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 208000004371 toothache Diseases 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 238000011269 treatment regimen Methods 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
- CVZIHNYAZLXRRS-HNNXBMFYSA-N (3s)-4-{[4-(but-2-ynyloxy)phenyl]sulfonyl}-n-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide Chemical compound C1=CC(OCC#CC)=CC=C1S(=O)(=O)N1[C@@H](C(=O)NO)C(C)(C)SCC1 CVZIHNYAZLXRRS-HNNXBMFYSA-N 0.000 description 1
- VOMHFFCEDKOLBR-RNFKYSJUSA-N (4r,4ar,7s,7ar,12bs)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCCN1CCOCC1 VOMHFFCEDKOLBR-RNFKYSJUSA-N 0.000 description 1
- WRRSFOZOETZUPG-FFHNEAJVSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC WRRSFOZOETZUPG-FFHNEAJVSA-N 0.000 description 1
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- GLCFWAYXPRBRNU-UHFFFAOYSA-N 1-(1-adamantyl)-2-aminoethanol Chemical compound C1C(C2)CC3CC2CC1(C(O)CN)C3 GLCFWAYXPRBRNU-UHFFFAOYSA-N 0.000 description 1
- FEALJKFIUQDJAV-UHFFFAOYSA-N 1-(aminomethyl)cyclopentan-1-ol Chemical compound NCC1(O)CCCC1 FEALJKFIUQDJAV-UHFFFAOYSA-N 0.000 description 1
- DFGJQHHGOXIWRM-UHFFFAOYSA-N 1-(trifluoromethyl)indole-3-carboxamide Chemical compound FC(F)(F)N1C=C(C2=CC=CC=C12)C(=O)N DFGJQHHGOXIWRM-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JRUUKWFSWAHVDA-UHFFFAOYSA-N 1-pyridin-3-ylcyclohexane-1-carbonitrile Chemical compound C=1C=CN=CC=1C1(C#N)CCCCC1 JRUUKWFSWAHVDA-UHFFFAOYSA-N 0.000 description 1
- NPFARWZUZNGMCY-UHFFFAOYSA-N 1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxylic acid Chemical compound C12=CC=CC(C(F)(F)F)=C2C(C(=O)O)=CN1C1=NC=CC=N1 NPFARWZUZNGMCY-UHFFFAOYSA-N 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
- GWNVDXQDILPJIG-CCHJCNDSSA-N 11-trans-Leukotriene C4 Chemical compound CCCCC\C=C/C\C=C\C=C\C=C\[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-CCHJCNDSSA-N 0.000 description 1
- JSOVGYMVTPPEND-UHFFFAOYSA-N 16-methylheptadecyl 2,2-dimethylpropanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C(C)(C)C JSOVGYMVTPPEND-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- TXQAZWIBPGKHOX-UHFFFAOYSA-N 1H-indol-3-amine Chemical compound C1=CC=C2C(N)=CNC2=C1 TXQAZWIBPGKHOX-UHFFFAOYSA-N 0.000 description 1
- RHRYWWVGUVEZRJ-UHFFFAOYSA-N 2,3-diphenylpropylamine Chemical compound C=1C=CC=CC=1C(CN)CC1=CC=CC=C1 RHRYWWVGUVEZRJ-UHFFFAOYSA-N 0.000 description 1
- AOTQGWFNFTVXNQ-UHFFFAOYSA-N 2-(1-adamantyl)acetic acid Chemical compound C1C(C2)CC3CC2CC1(CC(=O)O)C3 AOTQGWFNFTVXNQ-UHFFFAOYSA-N 0.000 description 1
- SNJMEUDNDRSJAS-UHFFFAOYSA-N 2-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(CCN)C3 SNJMEUDNDRSJAS-UHFFFAOYSA-N 0.000 description 1
- ITRNQMJXZUWZQL-UHFFFAOYSA-N 2-(2-bromophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1Br ITRNQMJXZUWZQL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ZSZCXAOQVBEPME-UHFFFAOYSA-N 2-(4-bromophenyl)ethanamine Chemical compound NCCC1=CC=C(Br)C=C1 ZSZCXAOQVBEPME-UHFFFAOYSA-N 0.000 description 1
- ZGOBGVMDCXQRKY-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methylpentan-1-amine Chemical compound CC(C)CC(CN)C1=CC=C(Cl)C=C1 ZGOBGVMDCXQRKY-UHFFFAOYSA-N 0.000 description 1
- MCCZYKLMBDYGFB-UHFFFAOYSA-N 2-(4-chlorophenyl)pentan-1-amine Chemical compound CCCC(CN)C1=CC=C(Cl)C=C1 MCCZYKLMBDYGFB-UHFFFAOYSA-N 0.000 description 1
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 1
- JDIPKQBKSBWIKU-UHFFFAOYSA-N 2-(chloromethyl)-1-methylimidazole;hydrochloride Chemical compound Cl.CN1C=CN=C1CCl JDIPKQBKSBWIKU-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- AMRBZKOCOOPYNY-QXMHVHEDSA-N 2-[dimethyl-[(z)-octadec-9-enyl]azaniumyl]acetate Chemical compound CCCCCCCC\C=C/CCCCCCCC[N+](C)(C)CC([O-])=O AMRBZKOCOOPYNY-QXMHVHEDSA-N 0.000 description 1
- VKNASXZDGZNEDA-UHFFFAOYSA-N 2-cyanoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC#N VKNASXZDGZNEDA-UHFFFAOYSA-N 0.000 description 1
- RDHLDAJFFHIZAT-UHFFFAOYSA-N 2-cyclohexyl-2-phenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1CCCCC1 RDHLDAJFFHIZAT-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- SQMNYSQPHYHTSO-UHFFFAOYSA-N 2-phenylpentan-1-amine Chemical compound CCCC(CN)C1=CC=CC=C1 SQMNYSQPHYHTSO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OIPHWUPMXHQWLR-UHFFFAOYSA-N 2-pyridin-3-ylacetonitrile Chemical compound N#CCC1=CC=CN=C1 OIPHWUPMXHQWLR-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
- LMGLILPGKZPDAX-UHFFFAOYSA-N 3-cyclopentyl-2-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CN)CC1CCCC1 LMGLILPGKZPDAX-UHFFFAOYSA-N 0.000 description 1
- IYNWSQDZXMGGGI-NUEKZKHPSA-N 3-hydroxymorphinan Chemical compound C1CCC[C@H]2[C@H]3CC4=CC=C(O)C=C4[C@]21CCN3 IYNWSQDZXMGGGI-NUEKZKHPSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
- HJMCIHLESAJJQL-UHFFFAOYSA-N 3-phenylbutan-1-amine Chemical compound NCCC(C)C1=CC=CC=C1 HJMCIHLESAJJQL-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 1
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 1
- FBTAUFARIAJZFV-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindol-3-amine Chemical compound C12=CC=CC(Cl)=C2C(N)=CN1C1=NC=CC=N1 FBTAUFARIAJZFV-UHFFFAOYSA-N 0.000 description 1
- SVLZRCRXNHITBY-UHFFFAOYSA-N 4-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1C=CN2 SVLZRCRXNHITBY-UHFFFAOYSA-N 0.000 description 1
- HNTZVGMWXCFCTA-UHFFFAOYSA-N 4-chloro-1h-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CC=NC2=C1C=CN2 HNTZVGMWXCFCTA-UHFFFAOYSA-N 0.000 description 1
- VEEYSQAYZKOZIT-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 VEEYSQAYZKOZIT-UHFFFAOYSA-N 0.000 description 1
- KEZICJUVFFKBAY-UHFFFAOYSA-N 4-methyl-2-(4-methylphenyl)pentan-1-amine Chemical compound CC(C)CC(CN)C1=CC=C(C)C=C1 KEZICJUVFFKBAY-UHFFFAOYSA-N 0.000 description 1
- QVGYRSNAMPKOGB-UHFFFAOYSA-N 4-methyl-2-pyridin-3-ylpentan-1-amine Chemical compound CC(C)CC(CN)C1=CC=CN=C1 QVGYRSNAMPKOGB-UHFFFAOYSA-N 0.000 description 1
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 206010027654 Allergic conditions Diseases 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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 208000035939 Alveolitis allergic Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 206010069632 Bladder dysfunction Diseases 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 206010005949 Bone cancer Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 1
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 1
- 229940124292 CD20 monoclonal antibody Drugs 0.000 description 1
- 229940127597 CGRP antagonist Drugs 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- 229940122444 Chemokine receptor antagonist Drugs 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- BDLSDHWCOJPHIE-KFUGMXNISA-N Codeine N-oxide Chemical compound C([C@H]1[C@H]([N@@+](CC[C@@]112)(C)[O-])C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC BDLSDHWCOJPHIE-KFUGMXNISA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 108010074922 Cytochrome P-450 CYP1A2 Proteins 0.000 description 1
- 108010026925 Cytochrome P-450 CYP2C19 Proteins 0.000 description 1
- 108010000543 Cytochrome P-450 CYP2C9 Proteins 0.000 description 1
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 description 1
- 108010001202 Cytochrome P-450 CYP2E1 Proteins 0.000 description 1
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 102100026533 Cytochrome P450 1A2 Human genes 0.000 description 1
- 102100036194 Cytochrome P450 2A6 Human genes 0.000 description 1
- 102100029363 Cytochrome P450 2C19 Human genes 0.000 description 1
- 102100029358 Cytochrome P450 2C9 Human genes 0.000 description 1
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 description 1
- 102100024889 Cytochrome P450 2E1 Human genes 0.000 description 1
- 102100039205 Cytochrome P450 3A4 Human genes 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 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 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 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
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- 206010065563 Eosinophilic bronchitis Diseases 0.000 description 1
- 206010014989 Epidermolysis bullosa Diseases 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 description 1
- KJTKYGFGPQSRRA-UHFFFAOYSA-N Etoxeridine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(CCOCCO)CC1 KJTKYGFGPQSRRA-UHFFFAOYSA-N 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- 208000034347 Faecal incontinence Diseases 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- 206010016228 Fasciitis Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- OZLGRUXZXMRXGP-UHFFFAOYSA-N Fluo-3 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)N(CC(O)=O)CC(O)=O)=C1 OZLGRUXZXMRXGP-UHFFFAOYSA-N 0.000 description 1
- OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000014540 Functional gastrointestinal disease Diseases 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 208000007465 Giant cell arteritis Diseases 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 208000024869 Goodpasture syndrome Diseases 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010063491 Herpes zoster oticus Diseases 0.000 description 1
- 101000875170 Homo sapiens Cytochrome P450 2A6 Proteins 0.000 description 1
- 101001098175 Homo sapiens P2X purinoceptor 7 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 208000035154 Hyperesthesia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 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
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 102100022339 Integrin alpha-L Human genes 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
- 102000010781 Interleukin-6 Receptors Human genes 0.000 description 1
- 108010038501 Interleukin-6 Receptors Proteins 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- 208000009388 Job Syndrome Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 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 1
- 208000007914 Labor Pain Diseases 0.000 description 1
- 208000035945 Labour pain Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 208000004852 Lung Injury Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical class [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- 206010027940 Mood altered Diseases 0.000 description 1
- AMAPEXTUMXQULJ-APQDOHRLSA-N Morphine N-oxide Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)(=O)[C@@H]3CC5=CC=C4O AMAPEXTUMXQULJ-APQDOHRLSA-N 0.000 description 1
- 208000002472 Morton Neuroma Diseases 0.000 description 1
- 208000020059 Morton neuralgia Diseases 0.000 description 1
- 201000002795 Muckle-Wells syndrome Diseases 0.000 description 1
- 208000006670 Multiple fractures Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000030858 Myofascial Pain Syndromes Diseases 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 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
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-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
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 1
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 1
- VWCUGCYZZGRKEE-UHFFFAOYSA-N Noracymethadol Chemical compound C=1C=CC=CC=1C(CC(C)NC)(C(OC(C)=O)CC)C1=CC=CC=C1 VWCUGCYZZGRKEE-UHFFFAOYSA-N 0.000 description 1
- ONBWJWYUHXVEJS-ZTYRTETDSA-N Normorphine Chemical compound C([C@@H](NCC1)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ONBWJWYUHXVEJS-ZTYRTETDSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
- LCAHPIFLPICNRW-SVYNMNNPSA-N Oxymetebanol Chemical compound C1[C@H](O)CC[C@@]2(O)[C@H]3CC4=CC=C(OC)C(OC)=C4[C@]21CCN3C LCAHPIFLPICNRW-SVYNMNNPSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000000450 Pelvic Pain Diseases 0.000 description 1
- 206010034277 Pemphigoid Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010035742 Pneumonitis Diseases 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920001100 Polydextrose Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
- 229920000289 Polyquaternium Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001219 Polysorbate 40 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 206010037394 Pulmonary haemorrhage Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101001098238 Rattus norvegicus P2X purinoceptor 7 Proteins 0.000 description 1
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- 206010039094 Rhinitis perennial Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 208000009359 Sezary Syndrome Diseases 0.000 description 1
- 208000021388 Sezary disease Diseases 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010054874 Sphenopalatine neuralgia Diseases 0.000 description 1
- 208000003589 Spider Bites Diseases 0.000 description 1
- 208000006045 Spondylarthropathies Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229930186949 TCA Natural products 0.000 description 1
- 229920002253 Tannate Polymers 0.000 description 1
- 206010043269 Tension headache Diseases 0.000 description 1
- 208000008548 Tension-Type Headache Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 206010048873 Traumatic arthritis Diseases 0.000 description 1
- 206010069363 Traumatic lung injury Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010046542 Urinary hesitation Diseases 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- ULHRKLSNHXXJLO-UHFFFAOYSA-L Yo-Pro-1 Chemical compound [I-].[I-].C1=CC=C2C(C=C3N(C4=CC=CC=C4O3)C)=CC=[N+](CCC[N+](C)(C)C)C2=C1 ULHRKLSNHXXJLO-UHFFFAOYSA-L 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
- 229920002494 Zein Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- ODEGQXRCQDVXSJ-RHSMWYFYSA-N [(3r,4r)-3-ethyl-1-methyl-4-phenylpiperidin-4-yl] propanoate Chemical compound CC[C@@H]1CN(C)CC[C@]1(OC(=O)CC)C1=CC=CC=C1 ODEGQXRCQDVXSJ-RHSMWYFYSA-N 0.000 description 1
- UVAZQQHAVMNMHE-BBRMVZONSA-N [(3s,4s)-1,3-dimethyl-4-phenylpiperidin-4-yl] propanoate Chemical compound C=1C=CC=CC=1[C@]1(OC(=O)CC)CCN(C)C[C@@H]1C UVAZQQHAVMNMHE-BBRMVZONSA-N 0.000 description 1
- ILBGUXQOPBTXLD-DNJOTXNNSA-N [(4r,4ar,7s,7ar,12bs)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-yl] methanesulfonate Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OS(C)(=O)=O ILBGUXQOPBTXLD-DNJOTXNNSA-N 0.000 description 1
- SFGGQMODVXPZAB-FIBQRRHKSA-N [4-[(2S,3R,4S,5R)-2-(6-aminopurin-9-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonyl]phenyl]-phenylmethanone Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)O[C@H](CO)[C@@H](O)[C@H]1O SFGGQMODVXPZAB-FIBQRRHKSA-N 0.000 description 1
- 229960003697 abatacept Drugs 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- LFYBMMHFJIAKFE-PMEKXCSPSA-N acetorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2OC(C)=O LFYBMMHFJIAKFE-PMEKXCSPSA-N 0.000 description 1
- 229960002948 acetyldihydrocodeine Drugs 0.000 description 1
- LGGDXXJAGWBUSL-BKRJIHRRSA-N acetyldihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](OC(C)=O)[C@@H]1OC1=C2C3=CC=C1OC LGGDXXJAGWBUSL-BKRJIHRRSA-N 0.000 description 1
- XBMIVRRWGCYBTQ-UHFFFAOYSA-N acetylmethadol Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(OC(C)=O)CC)C1=CC=CC=C1 XBMIVRRWGCYBTQ-UHFFFAOYSA-N 0.000 description 1
- 229950005506 acetylmethadol Drugs 0.000 description 1
- QOMNQGZXFYNBNG-UHFFFAOYSA-N acetyloxymethyl 2-[2-[2-[5-[3-(acetyloxymethoxy)-2,7-difluoro-6-oxoxanthen-9-yl]-2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]-n-[2-(acetyloxymethoxy)-2-oxoethyl]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(F)C(=O)C=C3OC3=CC(OCOC(C)=O)=C(F)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O QOMNQGZXFYNBNG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229960002964 adalimumab Drugs 0.000 description 1
- QZWNXXINFABALM-UHFFFAOYSA-N adamantan-2-amine Chemical compound C1C(C2)CC3CC1C(N)C2C3 QZWNXXINFABALM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002593 adenosine A3 receptor agonist Substances 0.000 description 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229960002459 alefacept Drugs 0.000 description 1
- 229960001391 alfentanil Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 125000002355 alkine group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 208000002029 allergic contact dermatitis Diseases 0.000 description 1
- 206010053552 allodynia Diseases 0.000 description 1
- KGYFOSCXVAXULR-UHFFFAOYSA-N allylprodine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)CC1CC=C KGYFOSCXVAXULR-UHFFFAOYSA-N 0.000 description 1
- 229950004361 allylprodine Drugs 0.000 description 1
- ODEGQXRCQDVXSJ-WMLDXEAASA-N alphameprodine Chemical compound CC[C@H]1CN(C)CC[C@]1(OC(=O)CC)C1=CC=CC=C1 ODEGQXRCQDVXSJ-WMLDXEAASA-N 0.000 description 1
- 229950008739 alphameprodine Drugs 0.000 description 1
- QIRAYNIFEOXSPW-YLJYHZDGSA-N alphamethadol Chemical compound C=1C=CC=CC=1C(C[C@@H](C)N(C)C)([C@H](O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-YLJYHZDGSA-N 0.000 description 1
- 229950006873 alphamethadol Drugs 0.000 description 1
- 229960001349 alphaprodine Drugs 0.000 description 1
- UVAZQQHAVMNMHE-XJKSGUPXSA-N alphaprodine Chemical compound C=1C=CC=CC=1[C@@]1(OC(=O)CC)CCN(C)C[C@@H]1C UVAZQQHAVMNMHE-XJKSGUPXSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229920003144 amino alkyl methacrylate copolymer Polymers 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 229960004238 anakinra Drugs 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- LKYQLAWMNBFNJT-UHFFFAOYSA-N anileridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC1=CC=C(N)C=C1 LKYQLAWMNBFNJT-UHFFFAOYSA-N 0.000 description 1
- 229960002512 anileridine Drugs 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 206010003074 arachnoiditis Diseases 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000006472 autoimmune response Effects 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000012754 barrier agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- UVTBZAWTRVBTMK-UHFFFAOYSA-N benzethidine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCOCC1=CC=CC=C1 UVTBZAWTRVBTMK-UHFFFAOYSA-N 0.000 description 1
- 229950002302 benzethidine Drugs 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 1
- RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- XBMIVRRWGCYBTQ-GCJKJVERSA-N betacetylmethadol Chemical compound C=1C=CC=CC=1C(C[C@@H](C)N(C)C)([C@@H](OC(C)=O)CC)C1=CC=CC=C1 XBMIVRRWGCYBTQ-GCJKJVERSA-N 0.000 description 1
- 229950003254 betacetylmethadol Drugs 0.000 description 1
- 229950004879 betameprodine Drugs 0.000 description 1
- QIRAYNIFEOXSPW-XLIONFOSSA-N betamethadol Chemical compound C=1C=CC=CC=1C(C[C@@H](C)N(C)C)([C@@H](O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-XLIONFOSSA-N 0.000 description 1
- 229950003767 betamethadol Drugs 0.000 description 1
- 229950000011 betaprodine Drugs 0.000 description 1
- FLKWNFFCSSJANB-UHFFFAOYSA-N bezitramide Chemical compound O=C1N(C(=O)CC)C2=CC=CC=C2N1C(CC1)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 FLKWNFFCSSJANB-UHFFFAOYSA-N 0.000 description 1
- 229960004611 bezitramide Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 208000019664 bone resorption disease Diseases 0.000 description 1
- 201000007637 bowel dysfunction Diseases 0.000 description 1
- 210000003461 brachial plexus Anatomy 0.000 description 1
- 239000003152 bradykinin antagonist Substances 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 description 1
- 229960001113 butorphanol Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 201000002676 cerebral atherosclerosis Diseases 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229960003115 certolizumab pegol Drugs 0.000 description 1
- 229940073669 ceteareth 20 Drugs 0.000 description 1
- 229940073642 ceteareth-30 Drugs 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229940074979 cetyl palmitate Drugs 0.000 description 1
- 229940119217 chamomile extract Drugs 0.000 description 1
- 235000020221 chamomile extract Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002559 chemokine receptor antagonist Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 231100000505 clastogenic Toxicity 0.000 description 1
- 230000003541 clastogenic effect Effects 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- GPZLDQAEBHTMPG-UHFFFAOYSA-N clonitazene Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2N(CCN(CC)CC)C=1CC1=CC=C(Cl)C=C1 GPZLDQAEBHTMPG-UHFFFAOYSA-N 0.000 description 1
- 229950001604 clonitazene Drugs 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Natural products C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
- KIKLDWULAZATJG-YZZSNFJZSA-M codeine methylbromide Chemical compound [Br-].C([C@H]1[C@H]([N+](CC[C@@]112)(C)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC KIKLDWULAZATJG-YZZSNFJZSA-M 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940039116 combination diclofenac Drugs 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 208000012790 cranial neuralgia Diseases 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- CAOQEOHEZKVYOJ-UHFFFAOYSA-N cycloheptylmethanamine Chemical compound NCC1CCCCCC1 CAOQEOHEZKVYOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- VSKIOMHXEUHYSI-KNLIIKEYSA-N cyprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11C=C[C@]3([C@H](C1)C(C)(C)O)OC)CN2CC1CC1 VSKIOMHXEUHYSI-KNLIIKEYSA-N 0.000 description 1
- 229950011021 cyprenorphine Drugs 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003210 demyelinating effect Effects 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 229950003851 desomorphine Drugs 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- INUNXTSAACVKJS-OAQYLSRUSA-N dextromoramide Chemical compound C([C@@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-OAQYLSRUSA-N 0.000 description 1
- 229960003701 dextromoramide Drugs 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- NCXVKLDKUADJPV-PVHGPHFFSA-N diacetyldihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O NCXVKLDKUADJPV-PVHGPHFFSA-N 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- RXTHKWVSXOIHJS-UHFFFAOYSA-N diampromide Chemical compound C=1C=CC=CC=1N(C(=O)CC)CC(C)N(C)CCC1=CC=CC=C1 RXTHKWVSXOIHJS-UHFFFAOYSA-N 0.000 description 1
- 229950001059 diampromide Drugs 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 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
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- CBYWMRHUUVRIAF-UHFFFAOYSA-N diethylthiambutene Chemical compound C=1C=CSC=1C(=CC(C)N(CC)CC)C1=CC=CS1 CBYWMRHUUVRIAF-UHFFFAOYSA-N 0.000 description 1
- 229950009987 diethylthiambutene Drugs 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 description 1
- 229960000920 dihydrocodeine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- RHUWRJWFHUKVED-UHFFFAOYSA-N dimenoxadol Chemical compound C=1C=CC=CC=1C(C(=O)OCCN(C)C)(OCC)C1=CC=CC=C1 RHUWRJWFHUKVED-UHFFFAOYSA-N 0.000 description 1
- 229950011187 dimenoxadol Drugs 0.000 description 1
- QIRAYNIFEOXSPW-UHFFFAOYSA-N dimepheptanol Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-UHFFFAOYSA-N 0.000 description 1
- 229950004655 dimepheptanol Drugs 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- LQGIXNQCOXNCRP-UHFFFAOYSA-N dioxaphetyl butyrate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)CCN1CCOCC1 LQGIXNQCOXNCRP-UHFFFAOYSA-N 0.000 description 1
- 229950008972 dioxaphetyl butyrate Drugs 0.000 description 1
- HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 description 1
- 229960004192 diphenoxylate Drugs 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000001177 diphosphate Substances 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
- SVDHSZFEQYXRDC-UHFFFAOYSA-N dipipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCCCC1 SVDHSZFEQYXRDC-UHFFFAOYSA-N 0.000 description 1
- 229960002500 dipipanone Drugs 0.000 description 1
- 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 1
- 238000007907 direct compression Methods 0.000 description 1
- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229950005448 drotebanol Drugs 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 108010047482 ectoATPase Proteins 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 230000000668 effect on calcium Effects 0.000 description 1
- 238000002565 electrocardiography Methods 0.000 description 1
- 230000007831 electrophysiology Effects 0.000 description 1
- 238000002001 electrophysiology Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229950000206 estolate Drugs 0.000 description 1
- 229960000403 etanercept Drugs 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- WEHDKOIKSRMLEK-UHFFFAOYSA-N ethanesulfonic acid;2-hydroxyethanesulfonic acid Chemical compound CCS(O)(=O)=O.OCCS(O)(=O)=O WEHDKOIKSRMLEK-UHFFFAOYSA-N 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 229960005542 ethidium bromide Drugs 0.000 description 1
- QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- MORSAEFGQPDBKM-UHFFFAOYSA-N ethylmethylthiambutene Chemical compound C=1C=CSC=1C(=CC(C)N(C)CC)C1=CC=CS1 MORSAEFGQPDBKM-UHFFFAOYSA-N 0.000 description 1
- 229950006111 ethylmethylthiambutene Drugs 0.000 description 1
- 229960004578 ethylmorphine Drugs 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 229960005293 etodolac Drugs 0.000 description 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 1
- PXDBZSCGSQSKST-UHFFFAOYSA-N etonitazene Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC([N+]([O-])=O)=CC=C2N1CCN(CC)CC PXDBZSCGSQSKST-UHFFFAOYSA-N 0.000 description 1
- 229950004538 etonitazene Drugs 0.000 description 1
- 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 1
- 229960004945 etoricoxib Drugs 0.000 description 1
- CAHCBJPUTCKATP-FAWZKKEFSA-N etorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O CAHCBJPUTCKATP-FAWZKKEFSA-N 0.000 description 1
- 229950004155 etorphine Drugs 0.000 description 1
- 229950004151 etoxeridine Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 208000022195 farmer lung disease Diseases 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229960005341 fenoprofen calcium Drugs 0.000 description 1
- VHUXSAWXWSTUOD-UHFFFAOYSA-L fenoprofen calcium (anhydrous) Chemical compound [Ca+2].[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1.[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 VHUXSAWXWSTUOD-UHFFFAOYSA-L 0.000 description 1
- 230000003352 fibrogenic effect Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229960002390 flurbiprofen Drugs 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
- 229940050411 fumarate Drugs 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- YFHXZQPUBCBNIP-UHFFFAOYSA-N fura-2 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=3OC(=CC=3C=2)C=2OC(=CN=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 YFHXZQPUBCBNIP-UHFFFAOYSA-N 0.000 description 1
- NNCOZXNZFLUYGG-UHFFFAOYSA-N furethidine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCOCC1CCCO1 NNCOZXNZFLUYGG-UHFFFAOYSA-N 0.000 description 1
- 229950011066 furethidine Drugs 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 201000011349 geniculate herpes zoster Diseases 0.000 description 1
- 229960001731 gluceptate Drugs 0.000 description 1
- KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002327 glycerophospholipids Chemical class 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940074774 glycyrrhizinate Drugs 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 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
- 229940076085 gold Drugs 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 239000012676 herbal extract Substances 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 238000012203 high throughput assay Methods 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
- 229960000240 hydrocodone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- AABLHGPVOULICI-BRJGLHKUSA-N hydromorphinol Chemical compound O([C@H]1[C@H](CC[C@]23O)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O AABLHGPVOULICI-BRJGLHKUSA-N 0.000 description 1
- 229950008720 hydromorphinol Drugs 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 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
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- WTJBNMUWRKPFRS-UHFFFAOYSA-N hydroxypethidine Chemical compound C=1C=CC(O)=CC=1C1(C(=O)OCC)CCN(C)CC1 WTJBNMUWRKPFRS-UHFFFAOYSA-N 0.000 description 1
- 229950008496 hydroxypethidine Drugs 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 206010051040 hyper-IgE syndrome Diseases 0.000 description 1
- 230000004047 hyperresponsiveness Effects 0.000 description 1
- 230000000642 iatrogenic effect Effects 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000036260 idiopathic disease Diseases 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 102000006495 integrins Human genes 0.000 description 1
- 108010044426 integrins Proteins 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 102000044166 interleukin-18 binding protein Human genes 0.000 description 1
- 108010070145 interleukin-18 binding protein Proteins 0.000 description 1
- 230000008991 intestinal motility Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- IFKPLJWIEQBPGG-UHFFFAOYSA-N isomethadone Chemical compound C=1C=CC=CC=1C(C(C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-UHFFFAOYSA-N 0.000 description 1
- 229950009272 isomethadone Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 229960003029 ketobemidone Drugs 0.000 description 1
- 150000002576 ketones Chemical class 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
- 229940001447 lactate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960000681 leflunomide Drugs 0.000 description 1
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 description 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
- 229950004990 levomethorphan Drugs 0.000 description 1
- INUNXTSAACVKJS-NRFANRHFSA-N levomoramide Chemical compound C([C@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-NRFANRHFSA-N 0.000 description 1
- RCYBMSQOSGJZLO-BGWNEDDSSA-N levophenacylmorphan Chemical compound C([C@]12CCCC[C@H]1[C@H]1CC3=CC=C(C=C32)O)CN1CC(=O)C1=CC=CC=C1 RCYBMSQOSGJZLO-BGWNEDDSSA-N 0.000 description 1
- 229950007939 levophenacylmorphan Drugs 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- DLBFLQKQABVKGT-UHFFFAOYSA-L lucifer yellow dye Chemical compound [Li+].[Li+].[O-]S(=O)(=O)C1=CC(C(N(C(=O)NN)C2=O)=O)=C3C2=CC(S([O-])(=O)=O)=CC3=C1N DLBFLQKQABVKGT-UHFFFAOYSA-L 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 description 1
- 210000004086 maxillary sinus Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 229960001929 meloxicam Drugs 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 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
- 150000002739 metals Chemical class 0.000 description 1
- 229950009131 metazocine Drugs 0.000 description 1
- YGSVZRIZCHZUHB-COLVAYQJSA-N metazocine Chemical compound C1C2=CC=C(O)C=C2[C@]2(C)CCN(C)[C@@]1([H])[C@@H]2C YGSVZRIZCHZUHB-COLVAYQJSA-N 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- TYDICGHIMKQKRI-UHFFFAOYSA-N methyl 1-pyrimidin-2-ylindole-3-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=CN1C1=NC=CC=N1 TYDICGHIMKQKRI-UHFFFAOYSA-N 0.000 description 1
- GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 description 1
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- CUFWYVOFDYVCPM-GGNLRSJOSA-N methyldesorphine Chemical compound O([C@H]1C(=CC[C@H]23)C)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O CUFWYVOFDYVCPM-GGNLRSJOSA-N 0.000 description 1
- 229950008517 methyldesorphine Drugs 0.000 description 1
- 229950004631 methyldihydromorphine Drugs 0.000 description 1
- QKWBBJJDJIZUKM-XSSYPUMDSA-N methyldihydromorphine Chemical compound C([C@@H](N(CC1)C)[C@@H]2CC[C@@H]3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 QKWBBJJDJIZUKM-XSSYPUMDSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- NPZXCTIHHUUEEJ-CMKMFDCUSA-N metopon Chemical compound O([C@@]1(C)C(=O)CC[C@@H]23)C4=C5[C@@]13CCN(C)[C@@H]2CC5=CC=C4O NPZXCTIHHUUEEJ-CMKMFDCUSA-N 0.000 description 1
- 229950006080 metopon Drugs 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 244000309715 mini pig Species 0.000 description 1
- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 description 1
- 229960004023 minocycline Drugs 0.000 description 1
- 229960005249 misoprostol Drugs 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 230000007510 mood change Effects 0.000 description 1
- JDEDMCKQPKGSAX-UHFFFAOYSA-N morpheridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCN1CCOCC1 JDEDMCKQPKGSAX-UHFFFAOYSA-N 0.000 description 1
- 229950007193 morpheridine Drugs 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- GODGZZGKTZQSAL-VXFFQEMOSA-N myrophine Chemical compound C([C@@H]1[C@@H]2C=C[C@@H]([C@@H]3OC4=C5[C@]23CCN1C)OC(=O)CCCCCCCCCCCCC)C5=CC=C4OCC1=CC=CC=C1 GODGZZGKTZQSAL-VXFFQEMOSA-N 0.000 description 1
- 229950007471 myrophine Drugs 0.000 description 1
- BOUCRWJEKAGKKG-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxyphenyl]acetamide Chemical compound CCN(CC)CC1=CC(NC(C)=O)=CC=C1O BOUCRWJEKAGKKG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- AWZOOKHXPUMUIM-UHFFFAOYSA-N n-methyl-1-pyridin-3-ylcyclohexan-1-amine Chemical compound C=1C=CN=CC=1C1(NC)CCCCC1 AWZOOKHXPUMUIM-UHFFFAOYSA-N 0.000 description 1
- 229960004270 nabumetone Drugs 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000002105 nanoparticle Substances 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
- 229960003940 naproxen sodium Drugs 0.000 description 1
- CDBRNDSHEYLDJV-FVGYRXGTSA-M naproxen sodium Chemical compound [Na+].C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-FVGYRXGTSA-M 0.000 description 1
- UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 description 1
- 229960005254 naratriptan Drugs 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 239000004084 narcotic analgesic agent Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229960005027 natalizumab Drugs 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008035 nerve activity Effects 0.000 description 1
- 208000019382 nerve compression syndrome Diseases 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000035771 neuroregeneration Effects 0.000 description 1
- 208000000288 neurosarcoidosis Diseases 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- RYBGRHAWFUVMST-MJFIPZRTSA-N nicocodine Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC4=CC=C(C=5O[C@@H]1[C@@]2(C4=5)CCN3C)OC)C(=O)C1=CC=CN=C1 RYBGRHAWFUVMST-MJFIPZRTSA-N 0.000 description 1
- HNDXBGYRMHRUFN-CIVUWBIHSA-N nicomorphine Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)OC(=O)C=4C=NC=CC=4)O[C@@H]1[C@]52CCN3C)C(=O)C1=CC=CN=C1 HNDXBGYRMHRUFN-CIVUWBIHSA-N 0.000 description 1
- 229960004300 nicomorphine Drugs 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 208000037916 non-allergic rhinitis Diseases 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229950008848 noracymethadol Drugs 0.000 description 1
- 229950011519 norlevorphanol Drugs 0.000 description 1
- WCJFBSYALHQBSK-UHFFFAOYSA-N normethadone Chemical compound C=1C=CC=CC=1C(CCN(C)C)(C(=O)CC)C1=CC=CC=C1 WCJFBSYALHQBSK-UHFFFAOYSA-N 0.000 description 1
- 229960004013 normethadone Drugs 0.000 description 1
- 229950006134 normorphine Drugs 0.000 description 1
- WCDSHELZWCOTMI-UHFFFAOYSA-N norpipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CCN1CCCCC1 WCDSHELZWCOTMI-UHFFFAOYSA-N 0.000 description 1
- 229950007418 norpipanone Drugs 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000000014 opioid analgesic Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 210000001328 optic nerve Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 208000020629 overactive bladder Diseases 0.000 description 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
- 229960002739 oxaprozin Drugs 0.000 description 1
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 1
- 229960001816 oxcarbazepine Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940124583 pain medication Drugs 0.000 description 1
- 230000037324 pain perception Effects 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 208000012111 paraneoplastic syndrome Diseases 0.000 description 1
- 229960004662 parecoxib Drugs 0.000 description 1
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 1
- 229940069533 paregoric Drugs 0.000 description 1
- 239000008414 paregoric Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940100460 peg-100 stearate Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 208000030062 persistent idiopathic facial pain Diseases 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- LOXCOAXRHYDLOW-UHFFFAOYSA-N phenadoxone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCOCC1 LOXCOAXRHYDLOW-UHFFFAOYSA-N 0.000 description 1
- 229950004540 phenadoxone Drugs 0.000 description 1
- DHTRHEVNFFZCNU-OAHLLOKOSA-N phenampromide Chemical compound C([C@@H](C)N(C(=O)CC)C=1C=CC=CC=1)N1CCCCC1 DHTRHEVNFFZCNU-OAHLLOKOSA-N 0.000 description 1
- 229950007248 phenampromide Drugs 0.000 description 1
- ZQHYKVKNPWDQSL-KNXBSLHKSA-N phenazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CCC1=CC=CC=C1 ZQHYKVKNPWDQSL-KNXBSLHKSA-N 0.000 description 1
- 229960000897 phenazocine Drugs 0.000 description 1
- CFBQYWXPZVQQTN-QPTUXGOLSA-N phenomorphan Chemical compound C([C@]12CCCC[C@H]1[C@H]1CC3=CC=C(C=C32)O)CN1CCC1=CC=CC=C1 CFBQYWXPZVQQTN-QPTUXGOLSA-N 0.000 description 1
- 229950011496 phenomorphan Drugs 0.000 description 1
- IPOPQVVNCFQFRK-UHFFFAOYSA-N phenoperidine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(O)C1=CC=CC=C1 IPOPQVVNCFQFRK-UHFFFAOYSA-N 0.000 description 1
- 229960004315 phenoperidine Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229960002808 pholcodine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 238000005222 photoaffinity labeling Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- PXXKIYPSXYFATG-UHFFFAOYSA-N piminodine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCCNC1=CC=CC=C1 PXXKIYPSXYFATG-UHFFFAOYSA-N 0.000 description 1
- 229950006445 piminodine Drugs 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IHEHEFLXQFOQJO-UHFFFAOYSA-N piritramide Chemical compound C1CC(C(=O)N)(N2CCCCC2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 IHEHEFLXQFOQJO-UHFFFAOYSA-N 0.000 description 1
- 229960001286 piritramide Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 238000002616 plasmapheresis Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940101027 polysorbate 40 Drugs 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 238000010149 post-hoc-test Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940050962 powdered opium Drugs 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 description 1
- 229960002943 prednisolone sodium phosphate Drugs 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- XJKQCILVUHXVIQ-UHFFFAOYSA-N properidine Chemical compound C=1C=CC=CC=1C1(C(=O)OC(C)C)CCN(C)CC1 XJKQCILVUHXVIQ-UHFFFAOYSA-N 0.000 description 1
- 229950004345 properidine Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 229940032043 quaternium-52 Drugs 0.000 description 1
- INUNXTSAACVKJS-UHFFFAOYSA-N racemoramide Chemical compound C1CCCN1C(=O)C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(C)CN1CCOCC1 INUNXTSAACVKJS-UHFFFAOYSA-N 0.000 description 1
- 229950011009 racemorphan Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 208000036273 reactive airway disease Diseases 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960004641 rituximab Drugs 0.000 description 1
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 description 1
- 229960000425 rizatriptan Drugs 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000007771 sciatic neuropathy Diseases 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 210000001044 sensory neuron Anatomy 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000003521 serotonin 5-HT1 receptor agonist Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000003567 signal transduction assay Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 231100000188 sister chromatid exchange Toxicity 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003890 substance P antagonist Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004739 sufentanil Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 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
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- 206010043207 temporal arteritis Diseases 0.000 description 1
- 229950002757 teoclate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- RRJQTGHQFYTZOW-ILWKUFEGSA-N thebacon Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C=C(OC(C)=O)[C@@H]1OC1=C2C3=CC=C1OC RRJQTGHQFYTZOW-ILWKUFEGSA-N 0.000 description 1
- 229960004412 thebacon Drugs 0.000 description 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000003582 thrombocytopenic effect Effects 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 229960003989 tocilizumab Drugs 0.000 description 1
- 229960002044 tolmetin sodium Drugs 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000000844 transformation Methods 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 229950009395 trimeperidine Drugs 0.000 description 1
- UVITTYOJFDLOGI-KEYYUXOJSA-N trimeperidine Chemical compound C=1C=CC=CC=1[C@]1(OC(=O)CC)C[C@H](C)N(C)C[C@H]1C UVITTYOJFDLOGI-KEYYUXOJSA-N 0.000 description 1
- GUIWIPNQQLZJIE-UHFFFAOYSA-K tris[2-(2-hydroxyethoxy)ethyl]-octadecylazanium;phosphate Chemical compound [O-]P([O-])([O-])=O.CCCCCCCCCCCCCCCCCC[N+](CCOCCO)(CCOCCO)CCOCCO GUIWIPNQQLZJIE-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 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 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 238000007631 vascular surgery Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 102000038650 voltage-gated calcium channel activity Human genes 0.000 description 1
- 108091023044 voltage-gated calcium channel activity Proteins 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D487/04—Ortho-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
- A61P1/16—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
- 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
- A61P25/28—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95525007P | 2007-08-10 | 2007-08-10 | |
| US60/955,250 | 2007-08-10 | ||
| PCT/US2008/072760 WO2009023623A1 (en) | 2007-08-10 | 2008-08-11 | Heteroaryl amide analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2008286946A1 AU2008286946A1 (en) | 2009-02-19 |
| AU2008286946B2 true AU2008286946B2 (en) | 2013-11-21 |
Family
ID=40351102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008286946A Ceased AU2008286946B2 (en) | 2007-08-10 | 2008-08-11 | Heteroaryl amide analogues |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP2185560A4 (enExample) |
| JP (2) | JP2010535816A (enExample) |
| KR (1) | KR20100066422A (enExample) |
| CN (1) | CN101778850A (enExample) |
| AU (1) | AU2008286946B2 (enExample) |
| BR (1) | BRPI0812594A2 (enExample) |
| CA (1) | CA2691512A1 (enExample) |
| CO (1) | CO6251319A2 (enExample) |
| EA (1) | EA020332B1 (enExample) |
| IL (1) | IL202550A0 (enExample) |
| NZ (1) | NZ582056A (enExample) |
| SG (1) | SG183699A1 (enExample) |
| UA (1) | UA99729C2 (enExample) |
| WO (1) | WO2009023623A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2243772B1 (en) * | 2009-04-14 | 2012-01-18 | Affectis Pharmaceuticals AG | Novel P2X7R antagonists and their use |
| WO2012110190A1 (en) * | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012154967A1 (en) * | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| WO2012163792A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| KR101995088B1 (ko) | 2011-07-22 | 2019-07-02 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
| MX336247B (es) | 2012-01-20 | 2016-01-13 | Actelion Pharmaceuticals Ltd | Derivados de amida heterociclicos como antagonistas del receptor p2x7. |
| JOP20130213B1 (ar) * | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| US9718774B2 (en) * | 2012-12-12 | 2017-08-01 | Idorsia Pharmaceuticals Ltd | Indole carboxamide derivatives as P2X7 receptor antagonist |
| AR094053A1 (es) * | 2012-12-18 | 2015-07-08 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x₇ |
| KR102220847B1 (ko) | 2013-01-22 | 2021-02-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
| EP2956135B1 (en) | 2013-01-22 | 2016-11-16 | Actelion Pharmaceuticals Ltd. | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| CA2900302C (en) | 2013-02-19 | 2018-07-03 | Pfizer Inc. | Azabenzimidazole compounds as inhibitors of pde4 isozymes for the treatment of cns and other disorders |
| TWI644671B (zh) * | 2013-03-14 | 2018-12-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調節劑 |
| TWI627174B (zh) | 2013-03-14 | 2018-06-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調控劑 |
| WO2014152537A1 (en) | 2013-03-14 | 2014-09-25 | Janssen Pharmaceutica Nv | P2x7 modulators |
| JP6294953B2 (ja) | 2013-03-14 | 2018-03-14 | ヤンセン ファーマシューティカ エヌ．ベー． | Ｐ２ｘ７調節物質 |
| ES2644025T3 (es) * | 2013-07-17 | 2017-11-27 | Global Alliance For Tb Drug Development | Compuestos de azaindol, síntesis de los mismos, y procedimientos de uso de los mismos |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| WO2016012896A1 (en) | 2014-07-24 | 2016-01-28 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| CR20170035A (es) | 2014-08-06 | 2017-04-28 | Pfizer | Compuestos de imidazopiridazina |
| EA201790600A1 (ru) | 2014-09-12 | 2017-07-31 | Янссен Фармацевтика Нв | Модулирующие p2x7 n-ацил-триазолопиразины |
| JP6592510B2 (ja) | 2014-09-12 | 2019-10-16 | ヤンセン ファーマシューティカ エヌ．ベー． | Ｐ２ｘ７調節因子 |
| ES2883295T3 (es) | 2014-09-29 | 2021-12-07 | Takeda Pharmaceuticals Co | Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1h-indol-3-carboxamida |
| CN107207476B (zh) * | 2014-12-15 | 2021-03-19 | 默克专利有限公司 | 吲哚和氮杂吲哚衍生物及其用于神经退化性疾病中的用途 |
| JP6462493B2 (ja) | 2015-05-29 | 2019-01-30 | 株式会社デンソー | 進入判定装置、進入判定方法 |
| US20190016680A1 (en) | 2016-01-14 | 2019-01-17 | Beth Israel Deaconess Medical Center, Inc. | Mast-cell modulators and uses thereof |
| TW201819361A (zh) | 2016-09-03 | 2018-06-01 | 印度商托仁特生技有限公司 | 新穎吲唑化合物 |
| CN113164459B (zh) | 2018-09-28 | 2024-09-03 | 詹森药业有限公司 | 单酰基甘油脂肪酶调节剂 |
| WO2020065614A1 (en) | 2018-09-28 | 2020-04-02 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| ES3037365T3 (en) | 2019-09-30 | 2025-10-01 | Janssen Pharmaceutica Nv | Radiolabelled mgl pet ligands |
| BR112022019077A2 (pt) | 2020-03-26 | 2022-12-27 | Janssen Pharmaceutica Nv | Moduladores da monoacilglicerol lipase |
| WO2022062991A1 (zh) * | 2020-09-22 | 2022-03-31 | 苏州恩华生物医药科技有限公司 | 吲哚衍生物及其应用 |
| CN119156388A (zh) * | 2022-04-15 | 2024-12-17 | 海南先声再明医药股份有限公司 | 膜缔合酪氨酸和苏氨酸激酶抑制剂 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030199689A1 (en) * | 2001-11-22 | 2003-10-23 | Marc Nazare | New indole derivatives as factor Xa inhibitors |
| US20040116388A1 (en) * | 1999-10-07 | 2004-06-17 | Amgen Inc. | Kinase inhibitors |
| WO2004056768A2 (en) * | 2002-12-20 | 2004-07-08 | Bayer Healthcare Ag | Use of substituted 2,5-diamidoindoles for the treatment of urological diseases |
| WO2005014529A1 (en) * | 2003-08-08 | 2005-02-17 | Astrazeneca Ab | 2- adamantyl derivatives as p2x7 receptor antagonists. |
| AU2006271524A1 (en) * | 2005-07-22 | 2007-01-25 | Sanofi-Aventis | N-(heteroaryl)-1-heteroarylalkyl-1H-indole-2-carboxamide derivatives, preparation and use thereof |
| WO2007079239A2 (en) * | 2005-12-30 | 2007-07-12 | Acadia Pharmaceuticals Inc. | Bicyclic nitrogen compounds as modulators of ghrelin receptor and uses thereof |
| AU2007217474A1 (en) * | 2006-02-21 | 2007-08-30 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557342A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
| DE2931323A1 (de) * | 1979-08-02 | 1981-02-26 | Kali Chemie Pharma Gmbh | Neue n-aminoalkylindol-derivate und ihre salze |
| DE3131527A1 (de) * | 1981-08-08 | 1983-02-24 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5023265A (en) * | 1990-06-01 | 1991-06-11 | Schering Corporation | Substituted 1-H-pyrrolopyridine-3-carboxamides |
| TW229140B (enExample) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
| US5424329A (en) * | 1993-08-18 | 1995-06-13 | Warner-Lambert Company | Indole-2-carboxamides as inhibitors of cell adhesion |
| PT1042287E (pt) * | 1997-12-24 | 2005-08-31 | Aventis Pharma Gmbh | Derivados de indole como inibidores do factor xa |
| CZ20013608A3 (cs) * | 1999-04-09 | 2002-05-15 | Astrazeneca Ab | Adamantanové deriváty |
| US6653304B2 (en) * | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| US7112594B2 (en) * | 2000-08-09 | 2006-09-26 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| BR0211810A (pt) * | 2001-08-09 | 2004-08-24 | Ono Pharmaceutical Co | Derivados ácido carboxìlico e agente farmacêutico compreendendo os mesmos como ingrediente ativo |
| CA2499329C (en) * | 2002-10-03 | 2009-04-21 | F. Hoffmann-La Roche Ag | Indole-3-carboxamides as glucokinase (gk) activators |
| DE10253426B4 (de) * | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| FR2857966A1 (fr) * | 2003-07-24 | 2005-01-28 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| FR2874015B1 (fr) * | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| FR2880625B1 (fr) * | 2005-01-07 | 2007-03-09 | Sanofi Aventis Sa | Derives de n-(heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| TW200700387A (en) * | 2005-03-21 | 2007-01-01 | Akzo Nobel Nv | 1-benzylindole-2-carboxamide derivatives |
-
2008
- 2008-08-11 BR BRPI0812594-5A patent/BRPI0812594A2/pt not_active IP Right Cessation
- 2008-08-11 WO PCT/US2008/072760 patent/WO2009023623A1/en not_active Ceased
- 2008-08-11 EP EP08797591A patent/EP2185560A4/en not_active Withdrawn
- 2008-08-11 CA CA002691512A patent/CA2691512A1/en not_active Abandoned
- 2008-08-11 AU AU2008286946A patent/AU2008286946B2/en not_active Ceased
- 2008-08-11 UA UAA200913336A patent/UA99729C2/ru unknown
- 2008-08-11 NZ NZ582056A patent/NZ582056A/xx not_active IP Right Cessation
- 2008-08-11 CN CN200880021498A patent/CN101778850A/zh active Pending
- 2008-08-11 SG SG2012058533A patent/SG183699A1/en unknown
- 2008-08-11 EA EA200971085A patent/EA020332B1/ru not_active IP Right Cessation
- 2008-08-11 JP JP2010520343A patent/JP2010535816A/ja not_active Ceased
- 2008-08-11 KR KR1020097026704A patent/KR20100066422A/ko not_active Ceased
-
2009
- 2009-12-06 IL IL202550A patent/IL202550A0/en unknown
- 2009-12-22 CO CO09146587A patent/CO6251319A2/es not_active Application Discontinuation
-
2014
- 2014-11-25 JP JP2014238138A patent/JP2015110566A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040116388A1 (en) * | 1999-10-07 | 2004-06-17 | Amgen Inc. | Kinase inhibitors |
| US20030199689A1 (en) * | 2001-11-22 | 2003-10-23 | Marc Nazare | New indole derivatives as factor Xa inhibitors |
| WO2004056768A2 (en) * | 2002-12-20 | 2004-07-08 | Bayer Healthcare Ag | Use of substituted 2,5-diamidoindoles for the treatment of urological diseases |
| WO2005014529A1 (en) * | 2003-08-08 | 2005-02-17 | Astrazeneca Ab | 2- adamantyl derivatives as p2x7 receptor antagonists. |
| AU2006271524A1 (en) * | 2005-07-22 | 2007-01-25 | Sanofi-Aventis | N-(heteroaryl)-1-heteroarylalkyl-1H-indole-2-carboxamide derivatives, preparation and use thereof |
| WO2007079239A2 (en) * | 2005-12-30 | 2007-07-12 | Acadia Pharmaceuticals Inc. | Bicyclic nitrogen compounds as modulators of ghrelin receptor and uses thereof |
| AU2007217474A1 (en) * | 2006-02-21 | 2007-08-30 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| CAS Registry Number 717845-36-8, 28 July 2004 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010535816A (ja) | 2010-11-25 |
| IL202550A0 (en) | 2010-06-30 |
| BRPI0812594A2 (pt) | 2015-06-23 |
| JP2015110566A (ja) | 2015-06-18 |
| NZ582056A (en) | 2012-08-31 |
| EP2185560A1 (en) | 2010-05-19 |
| CO6251319A2 (es) | 2011-02-21 |
| SG183699A1 (en) | 2012-09-27 |
| EA020332B1 (ru) | 2014-10-30 |
| CN101778850A (zh) | 2010-07-14 |
| UA99729C2 (en) | 2012-09-25 |
| AU2008286946A1 (en) | 2009-02-19 |
| CA2691512A1 (en) | 2009-02-19 |
| EP2185560A4 (en) | 2011-10-05 |
| EA200971085A1 (ru) | 2010-06-30 |
| WO2009023623A1 (en) | 2009-02-19 |
| KR20100066422A (ko) | 2010-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2008286946B2 (en) | Heteroaryl amide analogues | |
| EP2178865B1 (en) | 5-membered heterocyclic amides and related compounds | |
| US20120190680A1 (en) | Heteroaryl Amide Analogues | |
| AU2008236649B2 (en) | Heteroaryl amide analogues as P2X7 antagonists | |
| WO2009108551A2 (en) | Heteroaryl amide analogues | |
| US8431593B2 (en) | Heteroaryl amide derivatives | |
| HK1142599A (en) | Heteroaryl amide analogues | |
| HK1139005A (en) | Heteroaryl amide derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |