ES2277149T3 - Derivados de piridina como moduladores de los receptores cb2. - Google Patents
Derivados de piridina como moduladores de los receptores cb2. Download PDFInfo
- Publication number
- ES2277149T3 ES2277149T3 ES03798193T ES03798193T ES2277149T3 ES 2277149 T3 ES2277149 T3 ES 2277149T3 ES 03798193 T ES03798193 T ES 03798193T ES 03798193 T ES03798193 T ES 03798193T ES 2277149 T3 ES2277149 T3 ES 2277149T3
- Authority
- ES
- Spain
- Prior art keywords
- nicotinamide
- phenylamino
- fluoro
- benzyl
- isopropyl
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 208000002193 Pain Diseases 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 230000036407 pain Effects 0.000 claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 47
- -1 pyrizinyl Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 39
- 239000007787 solid Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 239000002105 nanoparticle Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 208000004296 neuralgia Diseases 0.000 claims description 9
- 208000021722 neuropathic pain Diseases 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 208000008035 Back Pain Diseases 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 208000008930 Low Back Pain Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 208000026278 immune system disease Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- VIDYNNZIYZXSRO-UHFFFAOYSA-N 6-(2-cyano-3-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C)=C1C#N VIDYNNZIYZXSRO-UHFFFAOYSA-N 0.000 claims description 3
- DHUGSUNSVLTDTM-UHFFFAOYSA-N 6-(3-chloro-4-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(F)C(Cl)=C1 DHUGSUNSVLTDTM-UHFFFAOYSA-N 0.000 claims description 3
- HRFSPRYAKFJJPT-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 HRFSPRYAKFJJPT-UHFFFAOYSA-N 0.000 claims description 3
- 208000004550 Postoperative Pain Diseases 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- ZPBVSCOBIZAMAY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-propan-2-yl-6-[3-(trifluoromethyl)anilino]pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C(F)(F)F)=C1 ZPBVSCOBIZAMAY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- 238000001238 wet grinding Methods 0.000 claims description 3
- WDMOKDLVCSTFNC-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Cl)C=C1Cl WDMOKDLVCSTFNC-UHFFFAOYSA-N 0.000 claims description 2
- BFKNCTNMYFDMID-UHFFFAOYSA-N 6-(2-bromo-4-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Cl)C=C1Br BFKNCTNMYFDMID-UHFFFAOYSA-N 0.000 claims description 2
- ZNMDBXTURIVJPF-UHFFFAOYSA-N 6-(2-chloro-4-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(F)C=C1Cl ZNMDBXTURIVJPF-UHFFFAOYSA-N 0.000 claims description 2
- QMUGRIITPDZHKX-UHFFFAOYSA-N 6-(3-chloroanilino)-4-propan-2-yl-n-(pyrazin-2-ylmethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2N=CC=NC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 QMUGRIITPDZHKX-UHFFFAOYSA-N 0.000 claims description 2
- SDKISIZAFVGWHD-UHFFFAOYSA-N 6-(3-chloroanilino)-4-propan-2-yl-n-(pyrimidin-4-ylmethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2N=CN=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 SDKISIZAFVGWHD-UHFFFAOYSA-N 0.000 claims description 2
- DUKBDMDUKNYYRA-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(1h-imidazol-2-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2NC=CN=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 DUKBDMDUKNYYRA-UHFFFAOYSA-N 0.000 claims description 2
- JPJVFDVMKSDSDG-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(pyridin-4-ylmethyl)-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NCC=2C=CN=CC=2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 JPJVFDVMKSDSDG-UHFFFAOYSA-N 0.000 claims description 2
- BTNCAWGVLHXQOR-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-cyanophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(=CC=2)C#N)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 BTNCAWGVLHXQOR-UHFFFAOYSA-N 0.000 claims description 2
- DKQJJLLVNPYGAV-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(6-methylpyridin-3-yl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=NC(C)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 DKQJJLLVNPYGAV-UHFFFAOYSA-N 0.000 claims description 2
- KCHREVSBHQMREC-UHFFFAOYSA-N 6-(3-cyanoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C#N)=C1 KCHREVSBHQMREC-UHFFFAOYSA-N 0.000 claims description 2
- PRIPEPDGNHKGME-UHFFFAOYSA-N 6-(4-bromo-2-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C=C1Cl PRIPEPDGNHKGME-UHFFFAOYSA-N 0.000 claims description 2
- TWRHLZHSWILHMW-UHFFFAOYSA-N 6-(4-cyano-2-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(C#N)C=C1C TWRHLZHSWILHMW-UHFFFAOYSA-N 0.000 claims description 2
- ILBFOAHHEOOKIN-UHFFFAOYSA-N 6-(5-chloro-2-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC(Cl)=CC=C1F ILBFOAHHEOOKIN-UHFFFAOYSA-N 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JAXKYWPPYAKTOY-UHFFFAOYSA-N n-benzyl-6-(3-chloroanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 JAXKYWPPYAKTOY-UHFFFAOYSA-N 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 8
- AGFUWYJKOBBRAQ-UHFFFAOYSA-N 6-(2,3-dichloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C(=C(Cl)C=CC=3)Cl)=NC=2)C(F)(F)F)=C1 AGFUWYJKOBBRAQ-UHFFFAOYSA-N 0.000 claims 1
- QEELEYIYYNZWHY-UHFFFAOYSA-N 6-(2,3-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1Cl QEELEYIYYNZWHY-UHFFFAOYSA-N 0.000 claims 1
- IQZVRLBNWINOEK-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)Cl)=NC=2)C(F)(F)F)=C1 IQZVRLBNWINOEK-UHFFFAOYSA-N 0.000 claims 1
- HWNQNJHKBRTERT-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=C(Cl)C=C1Cl HWNQNJHKBRTERT-UHFFFAOYSA-N 0.000 claims 1
- NRDXXGDBTKBXNH-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(5-methyl-1h-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N1C(C)=NN=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=C(Cl)C=C1Cl NRDXXGDBTKBXNH-UHFFFAOYSA-N 0.000 claims 1
- DRQZONSJVITKLK-UHFFFAOYSA-N 6-(2,5-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC(Cl)=CC=C1Cl DRQZONSJVITKLK-UHFFFAOYSA-N 0.000 claims 1
- NRXGSRYKMDNZKI-UHFFFAOYSA-N 6-(2-bromo-3-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C)=C1Br NRXGSRYKMDNZKI-UHFFFAOYSA-N 0.000 claims 1
- WUMODQKVGZVZLD-UHFFFAOYSA-N 6-(3,4-dibromoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C(Br)=C1 WUMODQKVGZVZLD-UHFFFAOYSA-N 0.000 claims 1
- AVTVSPSKCYLHFQ-UHFFFAOYSA-N 6-(3,4-dichloroanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC=C(Cl)C(Cl)=C1 AVTVSPSKCYLHFQ-UHFFFAOYSA-N 0.000 claims 1
- DNIJEZAZQKQRBC-UHFFFAOYSA-N 6-(3,4-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=C(Cl)C(Cl)=C1 DNIJEZAZQKQRBC-UHFFFAOYSA-N 0.000 claims 1
- MPCIMWFMJARQKT-UHFFFAOYSA-N 6-(3,4-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Cl)C(Cl)=C1 MPCIMWFMJARQKT-UHFFFAOYSA-N 0.000 claims 1
- HRKMKMCUYMECGF-UHFFFAOYSA-N 6-(3,5-dichloroanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC(Cl)=CC(Cl)=C1 HRKMKMCUYMECGF-UHFFFAOYSA-N 0.000 claims 1
- UAAXHTVLOPPOBP-UHFFFAOYSA-N 6-(3,5-dichloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C=C(Cl)C=C(Cl)C=3)=NC=2)C(F)(F)F)=C1 UAAXHTVLOPPOBP-UHFFFAOYSA-N 0.000 claims 1
- BWKGUUVPOOQAIZ-UHFFFAOYSA-N 6-(3,5-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC(Cl)=CC(Cl)=C1 BWKGUUVPOOQAIZ-UHFFFAOYSA-N 0.000 claims 1
- TUCHVBGRFKSMKU-UHFFFAOYSA-N 6-(3-bromo-2-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Br)=C1C TUCHVBGRFKSMKU-UHFFFAOYSA-N 0.000 claims 1
- RYQTWSDBXGEAGT-UHFFFAOYSA-N 6-(3-bromoanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Br)=C1 RYQTWSDBXGEAGT-UHFFFAOYSA-N 0.000 claims 1
- VFMLUFXHDRTZRN-UHFFFAOYSA-N 6-(3-bromoanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C=C(Br)C=CC=3)=NC=2)C(F)(F)F)=C1 VFMLUFXHDRTZRN-UHFFFAOYSA-N 0.000 claims 1
- XOGVVEYHWCVGSM-UHFFFAOYSA-N 6-(3-bromoanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=CC(Br)=C1 XOGVVEYHWCVGSM-UHFFFAOYSA-N 0.000 claims 1
- UFTOTCPQMHYHOK-UHFFFAOYSA-N 6-(3-bromoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Br)=C1 UFTOTCPQMHYHOK-UHFFFAOYSA-N 0.000 claims 1
- FCTSNQOOVQLGMY-UHFFFAOYSA-N 6-(3-chloro-2-cyanoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1C#N FCTSNQOOVQLGMY-UHFFFAOYSA-N 0.000 claims 1
- BGZBIAFILWLYTM-UHFFFAOYSA-N 6-(3-chloro-2-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1F BGZBIAFILWLYTM-UHFFFAOYSA-N 0.000 claims 1
- WGUKLFUNAYJMGN-UHFFFAOYSA-N 6-(3-chloro-2-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1C WGUKLFUNAYJMGN-UHFFFAOYSA-N 0.000 claims 1
- ROZJAGSCPOQOOQ-UHFFFAOYSA-N 6-(3-chloro-4-cyanoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(C#N)C(Cl)=C1 ROZJAGSCPOQOOQ-UHFFFAOYSA-N 0.000 claims 1
- YKPKYYNOYNZLBQ-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 YKPKYYNOYNZLBQ-UHFFFAOYSA-N 0.000 claims 1
- VEUHPKLXFLZXHS-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CN=CC=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 VEUHPKLXFLZXHS-UHFFFAOYSA-N 0.000 claims 1
- BXKMCEJPIVJIRD-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(2,4-difluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C(=CC(F)=CC=2)F)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 BXKMCEJPIVJIRD-UHFFFAOYSA-N 0.000 claims 1
- GJBYIPKVNIWVAR-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C=C(Cl)C=CC=3)=NC=2)C(F)(F)F)=C1 GJBYIPKVNIWVAR-UHFFFAOYSA-N 0.000 claims 1
- TVIAHQJPTJEZGB-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(3,4-difluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=C(F)C(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 TVIAHQJPTJEZGB-UHFFFAOYSA-N 0.000 claims 1
- PXBAWBJBSAXHLC-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=CC(Cl)=C1 PXBAWBJBSAXHLC-UHFFFAOYSA-N 0.000 claims 1
- FFZDDZRSCGLWKR-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-methoxyphenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C(C(=C1)C(C)C)=CN=C1NC1=CC=CC(Cl)=C1 FFZDDZRSCGLWKR-UHFFFAOYSA-N 0.000 claims 1
- IZIPSOQEHUCTKE-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-methylsulfonylphenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 IZIPSOQEHUCTKE-UHFFFAOYSA-N 0.000 claims 1
- HYRKYWXFAKFPMY-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[[4-(methanesulfonamido)phenyl]methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(NS(C)(=O)=O)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 HYRKYWXFAKFPMY-UHFFFAOYSA-N 0.000 claims 1
- BBRSUOINQITLFY-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[[4-(methylcarbamoyl)phenyl]methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1CNC(=O)C(C(=C1)C(C)C)=CN=C1NC1=CC=CC(Cl)=C1 BBRSUOINQITLFY-UHFFFAOYSA-N 0.000 claims 1
- OJHDXFMFJVSWJC-UHFFFAOYSA-N 6-(3-fluoro-2-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(F)=C1C OJHDXFMFJVSWJC-UHFFFAOYSA-N 0.000 claims 1
- XQYTZSBNZOHBMO-UHFFFAOYSA-N 6-(3-fluoroanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound FC1=CC=CC(NC=2N=CC(=C(C=2)C(F)(F)F)C(=O)NCCC=2C=CC=CC=2)=C1 XQYTZSBNZOHBMO-UHFFFAOYSA-N 0.000 claims 1
- VQIZPWYQCKKDFU-UHFFFAOYSA-N 6-(3-fluoroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound FC1=CC=CC(NC=2N=CC(=C(C=2)C(F)(F)F)C(=O)NCC=2C=C(F)N=CC=2)=C1 VQIZPWYQCKKDFU-UHFFFAOYSA-N 0.000 claims 1
- FLTOUEYUVPCMJC-UHFFFAOYSA-N 6-(3-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=CC(F)=C1 FLTOUEYUVPCMJC-UHFFFAOYSA-N 0.000 claims 1
- RZSWYYQBASHEAC-UHFFFAOYSA-N 6-(3-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(F)=C1 RZSWYYQBASHEAC-UHFFFAOYSA-N 0.000 claims 1
- LZERLTKNOCTXIW-UHFFFAOYSA-N 6-(4-bromo-2-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C=C1F LZERLTKNOCTXIW-UHFFFAOYSA-N 0.000 claims 1
- HLWSLEBNKYXTHC-UHFFFAOYSA-N 6-(4-bromo-3-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C(Cl)=C1 HLWSLEBNKYXTHC-UHFFFAOYSA-N 0.000 claims 1
- BXVKJHSJWJKCOY-UHFFFAOYSA-N 6-(4-bromo-3-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C(F)=C1 BXVKJHSJWJKCOY-UHFFFAOYSA-N 0.000 claims 1
- SZAAPTHAZQUGNS-UHFFFAOYSA-N 6-(4-chloro-2-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Cl)C=C1F SZAAPTHAZQUGNS-UHFFFAOYSA-N 0.000 claims 1
- RLNVKTWJYSGKLP-UHFFFAOYSA-N 6-(4-chloro-2-methylanilino)-n-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=CC(Cl)=CC=C1NC1=CC(C(F)(F)F)=C(C(=O)NCC=2C=CN=CC=2)C=N1 RLNVKTWJYSGKLP-UHFFFAOYSA-N 0.000 claims 1
- PFLHNLAKSCSLGF-UHFFFAOYSA-N 6-(4-cyanoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(C#N)C=C1 PFLHNLAKSCSLGF-UHFFFAOYSA-N 0.000 claims 1
- LKMPOSUBGUXEHU-UHFFFAOYSA-N 6-(5-chloro-2-methylanilino)-n-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=CC=C(Cl)C=C1NC1=CC(C(F)(F)F)=C(C(=O)NCC=2C=CN=CC=2)C=N1 LKMPOSUBGUXEHU-UHFFFAOYSA-N 0.000 claims 1
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- COUPHHICYQEECM-UHFFFAOYSA-N n-[(4-acetamidophenyl)methyl]-6-(3-chloroanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(NC(C)=O)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 COUPHHICYQEECM-UHFFFAOYSA-N 0.000 claims 1
- OYKMWXAHPOBHBT-UHFFFAOYSA-N n-[(4-carbamoylphenyl)methyl]-6-(3-chloroanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(=CC=2)C(N)=O)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 OYKMWXAHPOBHBT-UHFFFAOYSA-N 0.000 claims 1
- NHYBGOHXNVKASF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-propan-2-yl-6-[3-(trifluoromethoxy)anilino]pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(OC(F)(F)F)=C1 NHYBGOHXNVKASF-UHFFFAOYSA-N 0.000 claims 1
- WUHKOJMCMAENRG-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-(3-methoxyanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound COC1=CC=CC(NC=2N=CC(=C(C(C)C)C=2)C(=O)NCC=2C=CC(F)=CC=2)=C1 WUHKOJMCMAENRG-UHFFFAOYSA-N 0.000 claims 1
- JCRHKODHLSRSBN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-(3-methylanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C)=C1 JCRHKODHLSRSBN-UHFFFAOYSA-N 0.000 claims 1
- CYBWMTCXDUAMQS-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-[2-methyl-3-(trifluoromethyl)anilino]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C(F)(F)F)=C1C CYBWMTCXDUAMQS-UHFFFAOYSA-N 0.000 claims 1
- VXPTYHVVESVEMP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-[2-methyl-5-(trifluoromethyl)anilino]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC(C(F)(F)F)=CC=C1C VXPTYHVVESVEMP-UHFFFAOYSA-N 0.000 claims 1
- SEJFHOKKUIEFOR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-[3-fluoro-4-(trifluoromethyl)anilino]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 SEJFHOKKUIEFOR-UHFFFAOYSA-N 0.000 claims 1
- NOAMUOQSBPUBNZ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-[4-fluoro-3-(trifluoromethyl)anilino]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(F)C(C(F)(F)F)=C1 NOAMUOQSBPUBNZ-UHFFFAOYSA-N 0.000 claims 1
- UYQPFYJSXUGLBL-UHFFFAOYSA-N n-benzyl-6-(3-chloroanilino)-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NCC=2C=CC=CC=2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 UYQPFYJSXUGLBL-UHFFFAOYSA-N 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 28
- 230000000694 effects Effects 0.000 abstract description 23
- 201000010099 disease Diseases 0.000 abstract description 20
- 102000018208 Cannabinoid Receptor Human genes 0.000 abstract description 6
- 108050007331 Cannabinoid receptor Proteins 0.000 abstract description 6
- 150000003222 pyridines Chemical class 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 48
- 238000000034 method Methods 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 229930003827 cannabinoid Natural products 0.000 description 26
- 239000003557 cannabinoid Substances 0.000 description 26
- 229940065144 cannabinoids Drugs 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 239000000556 agonist Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 15
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 101710187022 Cannabinoid receptor 2 Proteins 0.000 description 12
- 102100036214 Cannabinoid receptor 2 Human genes 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 102000005962 receptors Human genes 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 10
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 229960004756 ethanol Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 7
- 241000218236 Cannabis Species 0.000 description 7
- 206010012289 Dementia Diseases 0.000 description 7
- 206010061218 Inflammation Diseases 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 208000014674 injury Diseases 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 208000011580 syndromic disease Diseases 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 description 6
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- ZTOBILYWTYHOJB-LWXMCBIJSA-N 3',6'-bis[[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C2C3(C4=CC=CC=C4C(=O)O3)C3=CC=C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=C3OC2=C1 ZTOBILYWTYHOJB-LWXMCBIJSA-N 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- NAWRPXVSHPFPPJ-UHFFFAOYSA-N 6-(3-chloroanilino)-4-propan-2-ylpyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(C)C)=CC(NC=2C=C(Cl)C=CC=2)=N1 NAWRPXVSHPFPPJ-UHFFFAOYSA-N 0.000 description 4
- XFNXCRVABIREQR-UHFFFAOYSA-N 6-chloro-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)C1=CC(Cl)=NC=C1C(=O)NCC1=CC=C(F)C=C1 XFNXCRVABIREQR-UHFFFAOYSA-N 0.000 description 4
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 4
- 229930024421 Adenine Natural products 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 101000710899 Homo sapiens Cannabinoid receptor 1 Proteins 0.000 description 4
- 101000875075 Homo sapiens Cannabinoid receptor 2 Proteins 0.000 description 4
- 206010065390 Inflammatory pain Diseases 0.000 description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 4
- 229960000643 adenine Drugs 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 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 4
- 102000056693 human CNR2 Human genes 0.000 description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
- 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 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 229960003136 leucine Drugs 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 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 4
- 230000001537 neural effect Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229960004799 tryptophan Drugs 0.000 description 4
- 229940035893 uracil Drugs 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- CRZDNISJUXVSKX-UHFFFAOYSA-N 1h-imidazol-2-ylmethanamine Chemical compound NCC1=NC=CN1 CRZDNISJUXVSKX-UHFFFAOYSA-N 0.000 description 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 3
- JKIHDSIADUBKPU-UHFFFAOYSA-N 4-(aminomethyl)benzamide Chemical compound NCC1=CC=C(C(N)=O)C=C1 JKIHDSIADUBKPU-UHFFFAOYSA-N 0.000 description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 3
- OZDOIRKHBFXCPL-UHFFFAOYSA-N 6-(3-chloroanilino)-4-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound C1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(Cl)=C1 OZDOIRKHBFXCPL-UHFFFAOYSA-N 0.000 description 3
- BULUOEXUXOKCIG-UHFFFAOYSA-N 6-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)C=C1C(F)(F)F BULUOEXUXOKCIG-UHFFFAOYSA-N 0.000 description 3
- ADZFLGUYHNISSP-UHFFFAOYSA-N 6-chloro-n-[(4-fluorophenyl)methyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(Cl)N=C1 ADZFLGUYHNISSP-UHFFFAOYSA-N 0.000 description 3
- 206010001497 Agitation Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 208000010412 Glaucoma Diseases 0.000 description 3
- 208000004454 Hyperalgesia Diseases 0.000 description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 3
- 230000002519 immonomodulatory effect Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000011777 magnesium Chemical class 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- VOEJMUXITRAHPS-UHFFFAOYSA-N n,6-dimethylpyridin-3-amine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(C)N=C1 VOEJMUXITRAHPS-UHFFFAOYSA-N 0.000 description 3
- 230000004770 neurodegeneration Effects 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 229940127240 opiate Drugs 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 208000035824 paresthesia Diseases 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 108700012359 toxins Proteins 0.000 description 3
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- YBWWLMTWKLKDBQ-UHFFFAOYSA-N (2-fluoropyridin-4-yl)methanamine;dihydrochloride Chemical compound Cl.Cl.NCC1=CC=NC(F)=C1 YBWWLMTWKLKDBQ-UHFFFAOYSA-N 0.000 description 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PBBXXIZQTKRHRJ-UHFFFAOYSA-N 2-oxo-6-(trifluoromethyl)-3,4-dihydro-1h-pyridine-5-carboxylic acid Chemical compound OC(=O)C1=C(C(F)(F)F)NC(=O)CC1 PBBXXIZQTKRHRJ-UHFFFAOYSA-N 0.000 description 2
- XRVLSHWAKUDIPM-UHFFFAOYSA-N 4-(aminomethyl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(CN)C=C1 XRVLSHWAKUDIPM-UHFFFAOYSA-N 0.000 description 2
- QVTCEZINLKFYJJ-UHFFFAOYSA-N 4-(bromomethyl)-2-fluoropyridine Chemical compound FC1=CC(CBr)=CC=N1 QVTCEZINLKFYJJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 208000000187 Abnormal Reflex Diseases 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 101710112457 Exoglucanase Proteins 0.000 description 2
- 208000001640 Fibromyalgia Diseases 0.000 description 2
- 108091006027 G proteins Proteins 0.000 description 2
- 101150102561 GPA1 gene Proteins 0.000 description 2
- 102000030782 GTP binding Human genes 0.000 description 2
- 108091000058 GTP-Binding Proteins 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- 208000007882 Gastritis Diseases 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010018634 Gouty Arthritis Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000035154 Hyperesthesia Diseases 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 206010041250 Social phobia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000010040 Sprains and Strains Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010000210 abortion Diseases 0.000 description 2
- 231100000176 abortion Toxicity 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Chemical class 0.000 description 2
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000002759 chromosomal effect Effects 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000003291 dopaminomimetic effect Effects 0.000 description 2
- 201000006549 dyspepsia Diseases 0.000 description 2
- 208000024732 dysthymic disease Diseases 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000013100 final test Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- 206010020745 hyperreflexia Diseases 0.000 description 2
- 230000035859 hyperreflexia Effects 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 238000011534 incubation Methods 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
- 230000001939 inductive effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 208000024714 major depressive disease Diseases 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 2
- 229960004503 metoclopramide Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 230000002981 neuropathic effect Effects 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002600 positron emission tomography Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007261 sc medium Substances 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 2
- 239000000952 serotonin receptor agonist Substances 0.000 description 2
- 238000002603 single-photon emission computed tomography Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229960003708 sumatriptan Drugs 0.000 description 2
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 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
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
- 229960004688 venlafaxine Drugs 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- 210000005253 yeast cell Anatomy 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 description 1
- IDCXLYCLPHRSAZ-UHFFFAOYSA-N 1,5-diphenylpyrazole Chemical class C=1C=CC=CC=1N1N=CC=C1C1=CC=CC=C1 IDCXLYCLPHRSAZ-UHFFFAOYSA-N 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
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- PKOMYWHVCYHAHW-UHFFFAOYSA-N 2-amino-6-methylbenzonitrile Chemical compound CC1=CC=CC(N)=C1C#N PKOMYWHVCYHAHW-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- ZBFAXMKJADVOGH-UHFFFAOYSA-N 2-fluoro-4-methylpyridine Chemical compound CC1=CC=NC(F)=C1 ZBFAXMKJADVOGH-UHFFFAOYSA-N 0.000 description 1
- XGYCHIPEPHYUIH-UHFFFAOYSA-N 2-mdp Chemical compound C=1C=CC=CC=1C(O)(C(CN)C)C1=CC=CC=C1 XGYCHIPEPHYUIH-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OGBMWKQQWRTZMB-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCOCC2)C(C(F)(F)F)=CC=1NC1=CC=C(Cl)C=C1Cl OGBMWKQQWRTZMB-UHFFFAOYSA-N 0.000 description 1
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 1
- IGIWMZNCMHZTEX-UHFFFAOYSA-N 6-chloro-4-propan-2-ylpyridine-3-carboxylic acid Chemical compound CC(C)C1=CC(Cl)=NC=C1C(O)=O IGIWMZNCMHZTEX-UHFFFAOYSA-N 0.000 description 1
- FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 1
- PBLOYQAQGYUPCM-UHFFFAOYSA-N 6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C=N1 PBLOYQAQGYUPCM-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 108010060263 Adenosine A1 Receptor Proteins 0.000 description 1
- 102000030814 Adenosine A1 receptor Human genes 0.000 description 1
- 208000008811 Agoraphobia Diseases 0.000 description 1
- WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 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
- 208000035939 Alveolitis allergic Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 206010002650 Anorexia nervosa and bulimia Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000000412 Avitaminosis Diseases 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 102000010183 Bradykinin receptor Human genes 0.000 description 1
- 108050001736 Bradykinin receptor Proteins 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
- 206010006811 Bursitis Diseases 0.000 description 1
- PSXLCTPHDAEPLK-UHFFFAOYSA-N CC(C)[Mg] Chemical compound CC(C)[Mg] PSXLCTPHDAEPLK-UHFFFAOYSA-N 0.000 description 1
- UVOLYTDXHDXWJU-UHFFFAOYSA-N Cannabichromene Chemical compound C1=CC(C)(CCC=C(C)C)OC2=CC(CCCCC)=CC(O)=C21 UVOLYTDXHDXWJU-UHFFFAOYSA-N 0.000 description 1
- VBGLYOIFKLUMQG-UHFFFAOYSA-N Cannabinol Chemical compound C1=C(C)C=C2C3=C(O)C=C(CCCCC)C=C3OC(C)(C)C2=C1 VBGLYOIFKLUMQG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-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
- 208000011231 Crohn disease Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000027219 Deficiency disease Diseases 0.000 description 1
- 208000019505 Deglutition disease Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001539473 Euphoria Species 0.000 description 1
- 206010015535 Euphoric mood Diseases 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 201000011240 Frontotemporal dementia Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 108700007698 Genetic Terminator Regions Proteins 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 229940122165 Glycine receptor antagonist Drugs 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 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 1
- 206010019973 Herpes virus infection Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 206010021135 Hypovitaminosis Diseases 0.000 description 1
- 206010021143 Hypoxia 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
- 206010061216 Infarction Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-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
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 201000002481 Myositis Diseases 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 1
- 206010028836 Neck pain Diseases 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 description 1
- 206010062501 Non-cardiac chest pain Diseases 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 101150053131 PTGER3 gene Proteins 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 208000000450 Pelvic Pain Diseases 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 102100024448 Prostaglandin E2 receptor EP2 subtype Human genes 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 101150058615 Ptger1 gene Proteins 0.000 description 1
- 101150109738 Ptger4 gene Proteins 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010063897 Renal ischaemia Diseases 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- HJPOKQICBCJGHE-UHFFFAOYSA-J [C+4].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [C+4].[Cl-].[Cl-].[Cl-].[Cl-] HJPOKQICBCJGHE-UHFFFAOYSA-J 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 230000007488 abnormal function Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000009692 acute damage Effects 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 229960002133 almotriptan Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229960000959 amineptine Drugs 0.000 description 1
- ONNOFKFOZAJDHT-UHFFFAOYSA-N amineptine Chemical compound C1CC2=CC=CC=C2C(NCCCCCCC(=O)O)C2=CC=CC=C21 ONNOFKFOZAJDHT-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000002399 aphthous stomatitis Diseases 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit 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
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 208000025307 bipolar depression Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 1
- 208000020670 canker sore Diseases 0.000 description 1
- 229950011318 cannabidiol Drugs 0.000 description 1
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 description 1
- 239000003556 cannabinoid 2 receptor agonist Substances 0.000 description 1
- 229960003453 cannabinol Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- 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 1
- 230000008614 cellular interaction Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 208000012601 choreatic disease Diseases 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical class C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 description 1
- 229960003314 deracoxib Drugs 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 229960002069 diamorphine Drugs 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
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229960004242 dronabinol Drugs 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000009513 drug distribution Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000020595 eating behavior Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 229960002472 eletriptan Drugs 0.000 description 1
- PWVXXGRKLHYWKM-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 PWVXXGRKLHYWKM-LJQANCHMSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940073621 enbrel Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 201000003104 endogenous depression Diseases 0.000 description 1
- 239000006274 endogenous ligand Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 208000006881 esophagitis Diseases 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 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
- OJSFTALXCYKKFQ-YLJYHZDGSA-N femoxetine Chemical compound C1=CC(OC)=CC=C1OC[C@@H]1[C@@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-YLJYHZDGSA-N 0.000 description 1
- 229950003930 femoxetine Drugs 0.000 description 1
- 230000027950 fever generation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229960002284 frovatriptan Drugs 0.000 description 1
- XPSQPHWEGNHMSK-SECBINFHSA-N frovatriptan Chemical compound N1C2=CC=C(C(N)=O)C=C2C2=C1CC[C@@H](NC)C2 XPSQPHWEGNHMSK-SECBINFHSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000002430 glycine receptor antagonist Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 description 1
- 229960003727 granisetron Drugs 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 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 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 230000028996 humoral immune response Effects 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
- 150000004677 hydrates Chemical class 0.000 description 1
- 208000021731 hypoalgesia Diseases 0.000 description 1
- 230000036032 hypoalgesia Effects 0.000 description 1
- 208000034783 hypoesthesia Diseases 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229950002473 indalpine Drugs 0.000 description 1
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001848 lamotrigine Drugs 0.000 description 1
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 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
- 102000003835 leukotriene receptors Human genes 0.000 description 1
- 108090000146 leukotriene receptors Proteins 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000005976 liver dysfunction Effects 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- ONJSLAKTVIZUQS-UHFFFAOYSA-K manganese(3+);triacetate;dihydrate Chemical compound O.O.[Mn+3].CC([O-])=O.CC([O-])=O.CC([O-])=O ONJSLAKTVIZUQS-UHFFFAOYSA-K 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940071648 metered dose inhaler Drugs 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- BVCVKJWRLVSUJC-UHFFFAOYSA-N methyl 6-(3-chloroanilino)-4-(trifluoromethyl)pyridine-3-carboxylate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CN=C1NC1=CC=CC(Cl)=C1 BVCVKJWRLVSUJC-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001730 monoaminergic effect Effects 0.000 description 1
- 230000001095 motoneuron effect Effects 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 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
- WVHKSWDIRFGODT-UHFFFAOYSA-N n-cyclobutyl-6-(2,3-dichloroanilino)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NC2CCC2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1Cl WVHKSWDIRFGODT-UHFFFAOYSA-N 0.000 description 1
- VGKOARVVEXZTPU-UHFFFAOYSA-N n-methylpyrazin-2-amine Chemical compound CNC1=CN=CC=N1 VGKOARVVEXZTPU-UHFFFAOYSA-N 0.000 description 1
- VERCQLOBLOLFMW-UHFFFAOYSA-N n-methylpyrimidin-4-amine Chemical compound CNC1=CC=NC=N1 VERCQLOBLOLFMW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004270 nabumetone Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960005254 naratriptan Drugs 0.000 description 1
- AMKVXSZCKVJAGH-UHFFFAOYSA-N naratriptan Chemical compound C12=CC(CCS(=O)(=O)NC)=CC=C2NC=C1C1CCN(C)CC1 AMKVXSZCKVJAGH-UHFFFAOYSA-N 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 238000002610 neuroimaging Methods 0.000 description 1
- 230000003959 neuroinflammation Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000007171 neuropathology Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 208000025319 neurotic depression Diseases 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 230000001473 noxious 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
- 239000002674 ointment Substances 0.000 description 1
- 229960005343 ondansetron Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000003349 osteoarthritic effect Effects 0.000 description 1
- IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000003950 pathogenic mechanism Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000006194 pentinyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 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
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
- 229960003770 reboxetine Drugs 0.000 description 1
- 229940116176 remicade Drugs 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 229960000425 rizatriptan 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
- 229960000371 rofecoxib Drugs 0.000 description 1
- 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 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 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
- 230000036280 sedation Effects 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000003521 serotonin 5-HT1 receptor agonist Substances 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229960002004 valdecoxib Drugs 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
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 208000030401 vitamin deficiency disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1
- 229960002791 zimeldine Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229960001360 zolmitriptan Drugs 0.000 description 1
- ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Reproductive Health (AREA)
- Oncology (AREA)
- Anesthesiology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0222495 | 2002-09-27 | ||
| GBGB0222495.4A GB0222495D0 (en) | 2002-09-27 | 2002-09-27 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2277149T3 true ES2277149T3 (es) | 2007-07-01 |
Family
ID=9944906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03798193T Expired - Lifetime ES2277149T3 (es) | 2002-09-27 | 2003-09-25 | Derivados de piridina como moduladores de los receptores cb2. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20070129367A1 (enExample) |
| EP (1) | EP1562907B1 (enExample) |
| JP (1) | JP2006508065A (enExample) |
| AT (1) | ATE345329T1 (enExample) |
| AU (1) | AU2003276028A1 (enExample) |
| DE (1) | DE60309739T2 (enExample) |
| ES (1) | ES2277149T3 (enExample) |
| GB (1) | GB0222495D0 (enExample) |
| WO (1) | WO2004029027A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
| TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| EP1669348A4 (en) | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| GB0402356D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| GB0402357D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| GB0402355D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| JP4874958B2 (ja) | 2005-03-30 | 2012-02-15 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピリジン誘導体を含有する抗真菌剤 |
| JPWO2006129609A1 (ja) * | 2005-05-30 | 2009-01-08 | 塩野義製薬株式会社 | 2−ナフチルイミノ−5,5−ジ置換−1,3−チアジン誘導体 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| WO2007118041A1 (en) * | 2006-04-07 | 2007-10-18 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2081905B1 (en) | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
| EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| MX2009002888A (es) | 2006-09-25 | 2009-03-31 | Boehringer Ingelheim Int | Compuestos que modulan el receptor cb2. |
| FR2907784B1 (fr) * | 2006-10-27 | 2009-02-13 | Sod Conseils Rech Applic | Derives phenyliques et leur utilisation comme medicament |
| US9422235B2 (en) | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
| TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| CN102702185A (zh) | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
| JP5300225B2 (ja) | 2007-08-03 | 2013-09-25 | バイエル・クロップサイエンス・アーゲー | 除草剤トリアゾリルピリジンケトン類 |
| WO2009061652A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| JP2011520975A (ja) * | 2008-05-19 | 2011-07-21 | ユニヴァーシティ オブ テネシー リサーチ ファウンデーション,ザ | ピリミジンの非古典的カンナビノイド化合物及び関連する使用方法 |
| EP2299819A4 (en) * | 2008-05-19 | 2011-07-20 | Univ Tennessee Res Foundation | NONCLASSICAL PYRIDINE CANNABINOID COMPOUNDS AND ASSOCIATED METHODS FOR THEIR USE |
| WO2009143182A1 (en) * | 2008-05-19 | 2009-11-26 | University Of Tennessee Research Foundation, The | Pyrimidine classical cannabinoid compounds and related methods of use |
| US8349876B2 (en) * | 2008-05-19 | 2013-01-08 | The University Of Tennesee Research Foundation | Pyridine non-classical cannabinoid compounds and related methods of use |
| EP2299817A1 (en) * | 2008-05-19 | 2011-03-30 | The University of Tennessee Research Foundation | Pyridine classical cannabinoid compounds and related methods of use |
| US8476439B2 (en) | 2008-05-19 | 2013-07-02 | The University Of Tennessee Research Foundation | Pyridine classical cannabinoid compounds and related methods of use |
| EP2326629B1 (en) | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| NZ591111A (en) | 2008-09-25 | 2013-08-30 | Boehringer Ingelheim Int | Sulfonyl compounds which selectively modulate the cb2 receptor |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| MX2011010396A (es) | 2009-03-30 | 2011-10-24 | Astellas Pharma Inc | Compuesto de pirimidina. |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| US8383615B2 (en) | 2009-06-16 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Azetidine 2-carboxamide derivatives which modulate the CB2 receptor |
| US8541386B2 (en) | 2009-08-19 | 2013-09-24 | University Of South Florida | Cannabinoid 2 (CB2) receptor gene promoter and unique RNA transcripts in B cells and methods of use |
| EP2480544A1 (en) | 2009-09-22 | 2012-08-01 | Boehringer Ingelheim International GmbH | Compounds which selectively modulate the cb2 receptor |
| EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
| WO2011109324A1 (en) | 2010-03-05 | 2011-09-09 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the cb2 receptor |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cb2受容体を調節する化合物 |
| WO2012031817A1 (en) * | 2010-09-09 | 2012-03-15 | F. Hoffmann-La Roche Ag | Determination of abca1 protein levels in cells |
| US8552200B2 (en) * | 2010-10-20 | 2013-10-08 | Gruenenthal Gmbh | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
| AU2013351552A1 (en) * | 2012-11-28 | 2015-07-16 | Grünenthal GmbH | Substituted Amino-arylcarboxamides as KCNQ2/3 modulators |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| CN106565517B (zh) * | 2016-10-18 | 2018-08-17 | 湖南大学 | 一种由芳基甲烷衍生物和腈制备酰胺的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112820A (en) * | 1990-03-05 | 1992-05-12 | Sterling Drug Inc. | Anti-glaucoma compositions containing 2- and 3-aminomethyl-6-arylcarbonyl- or 6-phenylthio-2,3-dihydropyrrolo-(1,2,3-de)-1,4-benzoxazines and method of use thereof |
| CZ101496A3 (en) * | 1993-10-12 | 1996-11-13 | Du Pont Merck Pharma | N-alkyl-n-aryl-pyrimidinamines and derivatives thereof |
| FR2742148B1 (fr) * | 1995-12-08 | 1999-10-22 | Sanofi Sa | Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US6022884A (en) * | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| US7507767B2 (en) * | 2001-02-08 | 2009-03-24 | Schering Corporation | Cannabinoid receptor ligands |
-
2002
- 2002-09-27 GB GBGB0222495.4A patent/GB0222495D0/en not_active Ceased
-
2003
- 2003-09-25 WO PCT/EP2003/010935 patent/WO2004029027A1/en not_active Ceased
- 2003-09-25 US US10/528,592 patent/US20070129367A1/en not_active Abandoned
- 2003-09-25 EP EP03798193A patent/EP1562907B1/en not_active Expired - Lifetime
- 2003-09-25 AT AT03798193T patent/ATE345329T1/de not_active IP Right Cessation
- 2003-09-25 AU AU2003276028A patent/AU2003276028A1/en not_active Abandoned
- 2003-09-25 JP JP2004539059A patent/JP2006508065A/ja not_active Withdrawn
- 2003-09-25 DE DE60309739T patent/DE60309739T2/de not_active Expired - Fee Related
- 2003-09-25 ES ES03798193T patent/ES2277149T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004029027A1 (en) | 2004-04-08 |
| EP1562907B1 (en) | 2006-11-15 |
| DE60309739D1 (de) | 2006-12-28 |
| US20070129367A1 (en) | 2007-06-07 |
| AU2003276028A1 (en) | 2004-04-19 |
| EP1562907A1 (en) | 2005-08-17 |
| JP2006508065A (ja) | 2006-03-09 |
| ATE345329T1 (de) | 2006-12-15 |
| DE60309739T2 (de) | 2007-10-31 |
| GB0222495D0 (en) | 2002-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2277149T3 (es) | Derivados de piridina como moduladores de los receptores cb2. | |
| ES2295682T3 (es) | Derivados de pirimidina y su uso como modulares de cb2. | |
| EP1565442B1 (en) | Pyridine derivatives as cb2 receptor modulators | |
| JP4764823B2 (ja) | キナーゼ阻害剤としての1,6−二置換アザベンゾイミダゾールの調製 | |
| ES2273077T3 (es) | Derivados de 2-fenilamino-4-trifluorometil-5 (bencil- o piridin-4-il-metil) carbamoilpirimidina como moduladores selectivos del receptor cannabinoide cb2. | |
| US20080280952A1 (en) | Pyridine Derivatives as Connabinoid Receptor Modulators | |
| ES2313304T3 (es) | Derivados de piridina y su uso como moduladores del receptor cb2. | |
| US20080261977A1 (en) | Pyrimidine Derivatives as Cannabinoid Receptor Modulators | |
| BRPI0614272A2 (pt) | derivados de imidazopiridinas como ligantes de receptores canabinóides | |
| WO2005080349A1 (en) | Pyrimidine derivatives | |
| HK1079193B (en) | Pyrimidine derivatives and their use as cb2 modulators |