OA12910A - Pyrimidine derivatives and their use as CB2 modulators. - Google Patents
Pyrimidine derivatives and their use as CB2 modulators. Download PDFInfo
- Publication number
- OA12910A OA12910A OA1200500052A OA1200500052A OA12910A OA 12910 A OA12910 A OA 12910A OA 1200500052 A OA1200500052 A OA 1200500052A OA 1200500052 A OA1200500052 A OA 1200500052A OA 12910 A OA12910 A OA 12910A
- Authority
- OA
- OAPI
- Prior art keywords
- amide
- carboxylic acid
- trifluoromethyl
- pyrimidine
- chloro
- Prior art date
Links
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract 2
- 150000003230 pyrimidines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 249
- 208000002193 Pain Diseases 0.000 claims abstract description 47
- 230000036407 pain Effects 0.000 claims abstract description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 230000000694 effects Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- -1 3- azetidinyl Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000003557 cannabinoid Substances 0.000 claims description 20
- 229930003827 cannabinoid Natural products 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 201000001119 neuropathy Diseases 0.000 claims description 10
- 230000007823 neuropathy Effects 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 208000008930 Low Back Pain Diseases 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 5
- 206010058019 Cancer Pain Diseases 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 208000026278 immune system disease Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000008482 osteoarthritis 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 3
- 230000003387 muscular Effects 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 abstract description 29
- 201000010099 disease Diseases 0.000 abstract description 18
- 102000018208 Cannabinoid Receptor Human genes 0.000 abstract description 4
- 108050007331 Cannabinoid receptor Proteins 0.000 abstract description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 153
- 239000002253 acid Substances 0.000 description 103
- 150000001793 charged compounds Chemical class 0.000 description 95
- 239000000243 solution Substances 0.000 description 92
- 238000000034 method Methods 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 238000000746 purification Methods 0.000 description 44
- 239000000203 mixture Substances 0.000 description 40
- IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 37
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- LQNHRNOPWKZUSN-UHFFFAOYSA-N cyclobutylmethanamine Chemical compound NCC1CCC1 LQNHRNOPWKZUSN-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 238000001665 trituration Methods 0.000 description 20
- FADYEGZICLBRGO-UHFFFAOYSA-N 2-(3-chloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(Cl)=C1 FADYEGZICLBRGO-UHFFFAOYSA-N 0.000 description 19
- MPIDQAYDKXNYKN-UHFFFAOYSA-N 2-chloro-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)NCC1CCCCC1 MPIDQAYDKXNYKN-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- FJWSUGZHRNASOK-UHFFFAOYSA-N 2-chloro-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)NCC1CCOCC1 FJWSUGZHRNASOK-UHFFFAOYSA-N 0.000 description 17
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 17
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- MSXJLEPWWWZERM-UHFFFAOYSA-N cyclopentylmethanamine;hydrochloride Chemical compound Cl.NCC1CCCC1 MSXJLEPWWWZERM-UHFFFAOYSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- ZIQIQOUPRHPOIT-UHFFFAOYSA-N cyclobutylazanide Chemical compound [NH-]C1CCC1 ZIQIQOUPRHPOIT-UHFFFAOYSA-N 0.000 description 11
- JVZOVVGVPJVLSL-UHFFFAOYSA-N cyclobutylmethanamine;hydron;chloride Chemical compound Cl.NCC1CCC1 JVZOVVGVPJVLSL-UHFFFAOYSA-N 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- PQLYFRFMBGHLNM-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(Cl)C=C1Cl PQLYFRFMBGHLNM-UHFFFAOYSA-N 0.000 description 10
- DLEJUDNSXPIFFH-UHFFFAOYSA-N 2-chloro-n-(cyclobutylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)NCC1CCC1 DLEJUDNSXPIFFH-UHFFFAOYSA-N 0.000 description 10
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 10
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 10
- 101710187022 Cannabinoid receptor 2 Proteins 0.000 description 10
- 102100036214 Cannabinoid receptor 2 Human genes 0.000 description 10
- 229940065144 cannabinoids Drugs 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- ZXFXWQGJKSWHST-UHFFFAOYSA-N 2-(3-bromoanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(Br)=C1 ZXFXWQGJKSWHST-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000556 agonist Substances 0.000 description 8
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 8
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 8
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- 241000218236 Cannabis Species 0.000 description 7
- 206010012289 Dementia Diseases 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- MAIWNYOADJRNOB-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)N=C1C(F)(F)F MAIWNYOADJRNOB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 229960001407 sodium bicarbonate Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000001238 wet grinding Methods 0.000 description 6
- KQXSFPJFMQYBRL-UHFFFAOYSA-N 2-(2,5-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC(Cl)=CC=C1Cl KQXSFPJFMQYBRL-UHFFFAOYSA-N 0.000 description 5
- QXGCERAYJADHBM-UHFFFAOYSA-N 2-(3,4-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(Cl)C(Cl)=C1 QXGCERAYJADHBM-UHFFFAOYSA-N 0.000 description 5
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 description 5
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 206010065390 Inflammatory pain Diseases 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 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
- 230000001965 increasing effect Effects 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- IWHLPMBLJZJCJK-UHFFFAOYSA-N 1-cyclohexyl-n-methylmethanamine Chemical compound CNCC1CCCCC1 IWHLPMBLJZJCJK-UHFFFAOYSA-N 0.000 description 4
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 4
- LBYRNIWGLNLDFY-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC(Cl)=CC(Cl)=C1 LBYRNIWGLNLDFY-UHFFFAOYSA-N 0.000 description 4
- BTRSILVUNQWNDR-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(Cl)=O BTRSILVUNQWNDR-UHFFFAOYSA-N 0.000 description 4
- XWBTZHDDWRNOQH-UHFFFAOYSA-N 3-chloro-2-fluoroaniline Chemical compound NC1=CC=CC(Cl)=C1F XWBTZHDDWRNOQH-UHFFFAOYSA-N 0.000 description 4
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-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
- 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
- 208000019695 Migraine disease Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
- 239000005557 antagonist Substances 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 210000004899 c-terminal region Anatomy 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
- 239000002775 capsule Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002474 experimental method 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
- 125000005842 heteroatom Chemical group 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 239000012044 organic layer Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- XUSXTHMTOSFZII-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1(O)CCCCC1 XUSXTHMTOSFZII-UHFFFAOYSA-N 0.000 description 3
- AUJPIEFPTQXBNO-UHFFFAOYSA-N 2-(2,3-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(Cl)=C1Cl AUJPIEFPTQXBNO-UHFFFAOYSA-N 0.000 description 3
- LXVGNPSJDUFWIZ-UHFFFAOYSA-N 2-(4-cyanoanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(C#N)C=C1 LXVGNPSJDUFWIZ-UHFFFAOYSA-N 0.000 description 3
- YKPDYPPZLUZONK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1F YKPDYPPZLUZONK-UHFFFAOYSA-N 0.000 description 3
- ZFBKYGFPUCUYIF-UHFFFAOYSA-N 4-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C(Cl)=C1 ZFBKYGFPUCUYIF-UHFFFAOYSA-N 0.000 description 3
- INMZDDDQLHKGPF-UHFFFAOYSA-N 4-bromo-2-chloroaniline Chemical compound NC1=CC=C(Br)C=C1Cl INMZDDDQLHKGPF-UHFFFAOYSA-N 0.000 description 3
- GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 3
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000010412 Glaucoma Diseases 0.000 description 3
- 208000004454 Hyperalgesia Diseases 0.000 description 3
- 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 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 244000025272 Persea americana Species 0.000 description 3
- 235000008673 Persea americana Nutrition 0.000 description 3
- 206010041250 Social phobia Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000001537 neural effect Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 208000035824 paresthesia Diseases 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 3
- 229940035893 uracil Drugs 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
- XLXBMMXDVLSNGN-UHFFFAOYSA-N 1-cyclopentyl-n-methylmethanamine Chemical compound CNCC1CCCC1 XLXBMMXDVLSNGN-UHFFFAOYSA-N 0.000 description 2
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 2
- AGHKJHVEUMCYKH-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=C(Cl)C=CC=C1Cl AGHKJHVEUMCYKH-UHFFFAOYSA-N 0.000 description 2
- KRKHNXWLWCVRTH-UHFFFAOYSA-N 2-(3-chloroanilino)-n-(cyclobutylmethyl)-n-methyl-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound C=1N=C(NC=2C=C(Cl)C=CC=2)N=C(C(F)(F)F)C=1C(=O)N(C)CC1CCC1 KRKHNXWLWCVRTH-UHFFFAOYSA-N 0.000 description 2
- PLYTYCKXBGPUGY-UHFFFAOYSA-N 2-(3-chloroanilino)-n-(thian-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCSCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 PLYTYCKXBGPUGY-UHFFFAOYSA-N 0.000 description 2
- ZRGQAGNAUZVFMG-UHFFFAOYSA-N 2-(3-cyanoanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(C#N)=C1 ZRGQAGNAUZVFMG-UHFFFAOYSA-N 0.000 description 2
- YLOBUWJXXIXCCD-UHFFFAOYSA-N 2-(3-cyanoanilino)-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(C#N)=C1 YLOBUWJXXIXCCD-UHFFFAOYSA-N 0.000 description 2
- IFXGUPYPPGDEKM-UHFFFAOYSA-N 2-(3-methoxyanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound COC1=CC=CC(NC=2N=C(C(C(O)=O)=CN=2)C(F)(F)F)=C1 IFXGUPYPPGDEKM-UHFFFAOYSA-N 0.000 description 2
- GJBDJFIJHVQJOD-UHFFFAOYSA-N 2-(5-chloro-2-fluoroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC(Cl)=CC=C1F GJBDJFIJHVQJOD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- FMSXPVBLDQSTMV-UHFFFAOYSA-N 2-anilino-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC=C1 FMSXPVBLDQSTMV-UHFFFAOYSA-N 0.000 description 2
- SYTBIFURTZACKR-UHFFFAOYSA-N 2-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1Br SYTBIFURTZACKR-UHFFFAOYSA-N 0.000 description 2
- XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 2
- KQOIBXZRCYFZSO-UHFFFAOYSA-N 3,5-difluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1 KQOIBXZRCYFZSO-UHFFFAOYSA-N 0.000 description 2
- CRRVZRDISHOQQL-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C(F)=C1 CRRVZRDISHOQQL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LNKBDFVSILQKSI-UHFFFAOYSA-N 4-Chloro-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1Cl LNKBDFVSILQKSI-UHFFFAOYSA-N 0.000 description 2
- CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 2
- JCYROOANFKVAIB-UHFFFAOYSA-N 5-chloro-2-fluoroaniline Chemical compound NC1=CC(Cl)=CC=C1F JCYROOANFKVAIB-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 2
- GUDPJHONHNSJBI-PMMFOGROSA-N C([ClH]([2H])([2H])([2H])([2H])[2H])(Cl)(Cl)[2H] Chemical compound C([ClH]([2H])([2H])([2H])([2H])[2H])(Cl)(Cl)[2H] GUDPJHONHNSJBI-PMMFOGROSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229940123549 Cannabinoid CB1 receptor agonist Drugs 0.000 description 2
- 229940123368 Cannabinoid CB2 receptor agonist Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 102000034353 G alpha subunit Human genes 0.000 description 2
- 108091006099 G alpha subunit 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
- 108700007698 Genetic Terminator Regions Proteins 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010018634 Gouty Arthritis Diseases 0.000 description 2
- 102100022087 Granzyme M Human genes 0.000 description 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- 208000037357 HIV infectious disease Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000900697 Homo sapiens Granzyme M Proteins 0.000 description 2
- 208000035154 Hyperesthesia 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
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
- 102100024448 Prostaglandin E2 receptor EP2 subtype Human genes 0.000 description 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 201000004810 Vascular dementia Diseases 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 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
- 206010003246 arthritis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000004429 atom Chemical group 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004556 brain Anatomy 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
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000003554 cannabinoid 1 receptor agonist Substances 0.000 description 2
- 239000003556 cannabinoid 2 receptor agonist Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000010261 cell growth 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
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000002759 chromosomal effect Effects 0.000 description 2
- 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 2
- 229940111134 coxibs Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 2
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 2
- 230000003291 dopaminomimetic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 230000028993 immune response Effects 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
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229960003136 leucine Drugs 0.000 description 2
- 239000006194 liquid suspension Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 206010027175 memory impairment Diseases 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- LIUZPQIQPGEOQW-UHFFFAOYSA-N methyl 2-(2,4-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound N1=C(C(F)(F)F)C(C(=O)OC)=CN=C1NC1=CC=C(Cl)C=C1Cl LIUZPQIQPGEOQW-UHFFFAOYSA-N 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
- HMPCNMJBHVBSEM-UHFFFAOYSA-N n-(cyclobutylmethyl)-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NCC1CCC1 HMPCNMJBHVBSEM-UHFFFAOYSA-N 0.000 description 2
- NJFPAJPTWUBRSO-UHFFFAOYSA-N n-(cyclopentylmethyl)-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NCC1CCCC1 NJFPAJPTWUBRSO-UHFFFAOYSA-N 0.000 description 2
- SFNWZPCZGMTGRQ-UHFFFAOYSA-N n-(cyclopentylmethyl)-2-(3-methoxyanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound COC1=CC=CC(NC=2N=C(C(C(=O)NCC3CCCC3)=CN=2)C(F)(F)F)=C1 SFNWZPCZGMTGRQ-UHFFFAOYSA-N 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
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000003566 oxetanyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 2
- 239000000952 serotonin receptor agonist Substances 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 230000000638 stimulation Effects 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
- 238000003786 synthesis reaction Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- AWCWSADJWHZJOL-UHFFFAOYSA-N thian-4-ylmethanamine Chemical compound NCC1CCSCC1 AWCWSADJWHZJOL-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 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
- 238000003325 tomography Methods 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 230000002103 transcriptional effect Effects 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229960004799 tryptophan Drugs 0.000 description 2
- 208000019553 vascular disease Diseases 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
- 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
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-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
- NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical group C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 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
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- IDCXLYCLPHRSAZ-UHFFFAOYSA-N 1,5-diphenylpyrazole Chemical compound C=1C=CC=CC=1N1N=CC=C1C1=CC=CC=C1 IDCXLYCLPHRSAZ-UHFFFAOYSA-N 0.000 description 1
- YRIMTMONXNUNNX-UHFFFAOYSA-N 1-cyclopentyl-n-methylmethanamine;hydrochloride Chemical compound Cl.CNCC1CCCC1 YRIMTMONXNUNNX-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 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
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- YCCQGFYAVUTQFK-UHFFFAOYSA-N 2,3-difluoroaniline Chemical compound NC1=CC=CC(F)=C1F YCCQGFYAVUTQFK-UHFFFAOYSA-N 0.000 description 1
- CJZDXHPGLMRYDM-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-n-(thian-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCSCC2)C(C(F)(F)F)=NC=1NC1=CC=C(Cl)C=C1Cl CJZDXHPGLMRYDM-UHFFFAOYSA-N 0.000 description 1
- XOPBKIYVXXKHML-UHFFFAOYSA-N 2-(2,5-dichloroanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCOCC2)C(C(F)(F)F)=NC=1NC1=CC(Cl)=CC=C1Cl XOPBKIYVXXKHML-UHFFFAOYSA-N 0.000 description 1
- JYBRSQPBHSZPNM-UHFFFAOYSA-N 2-(2-bromo-4-chloroanilino)-n-(cyclobutylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCC2)C(C(F)(F)F)=NC=1NC1=CC=C(Cl)C=C1Br JYBRSQPBHSZPNM-UHFFFAOYSA-N 0.000 description 1
- MHAQAUNLFOQTLZ-UHFFFAOYSA-N 2-(2-chloro-4-cyanoanilino)-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCCC2)C(C(F)(F)F)=NC=1NC1=CC=C(C#N)C=C1Cl MHAQAUNLFOQTLZ-UHFFFAOYSA-N 0.000 description 1
- KSZFICJZVIQOJN-UHFFFAOYSA-N 2-(2-chloro-4-fluoroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(F)C=C1Cl KSZFICJZVIQOJN-UHFFFAOYSA-N 0.000 description 1
- CPRPCUOGSZWUKM-UHFFFAOYSA-N 2-(2-chloro-4-methylanilino)-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound ClC1=CC(C)=CC=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCCCC1 CPRPCUOGSZWUKM-UHFFFAOYSA-N 0.000 description 1
- FCQIHWCDAKCBCU-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=C(Cl)C(NC=2N=C(C(C(=O)NCC3CCCC3)=CN=2)C(F)(F)F)=C1 FCQIHWCDAKCBCU-UHFFFAOYSA-N 0.000 description 1
- WBZIJIMCMDUDFO-UHFFFAOYSA-N 2-(3-bromoanilino)-n-(cyclopropylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Br)=C1 WBZIJIMCMDUDFO-UHFFFAOYSA-N 0.000 description 1
- IPGPGNHJZIAAFL-UHFFFAOYSA-N 2-(3-bromoanilino)-n-cyclobutyl-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NC2CCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Br)=C1 IPGPGNHJZIAAFL-UHFFFAOYSA-N 0.000 description 1
- QHIUANJQCLZXON-UHFFFAOYSA-N 2-(3-bromoanilino)-n-cyclopentyl-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Br)=C1 QHIUANJQCLZXON-UHFFFAOYSA-N 0.000 description 1
- GYWXGNDUDWZEJW-UHFFFAOYSA-N 2-(3-chloro-2-fluoroanilino)-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC1=C(Cl)C=CC=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCCC1 GYWXGNDUDWZEJW-UHFFFAOYSA-N 0.000 description 1
- RAFBDARNLQNMAT-UHFFFAOYSA-N 2-(3-chloro-4-cyanoanilino)-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=C(C#N)C(Cl)=C1 RAFBDARNLQNMAT-UHFFFAOYSA-N 0.000 description 1
- QBRRDUJEFJXFNB-UHFFFAOYSA-N 2-(3-chloro-4-cyanoanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCOCC2)C(C(F)(F)F)=NC=1NC1=CC=C(C#N)C(Cl)=C1 QBRRDUJEFJXFNB-UHFFFAOYSA-N 0.000 description 1
- XVLUHBNZQFZIIJ-UHFFFAOYSA-N 2-(3-chloro-4-fluoroanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCOCC1 XVLUHBNZQFZIIJ-UHFFFAOYSA-N 0.000 description 1
- ASWMSOMWPALYKM-UHFFFAOYSA-N 2-(3-chloroanilino)-n-(2-hydroxypropyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NCC(O)C)=CN=C1NC1=CC=CC(Cl)=C1 ASWMSOMWPALYKM-UHFFFAOYSA-N 0.000 description 1
- UBXLUQJENJXEJG-UHFFFAOYSA-N 2-(3-chloroanilino)-n-(3,3-dimethylbutyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(=O)NCCC(C)(C)C)=CN=C1NC1=CC=CC(Cl)=C1 UBXLUQJENJXEJG-UHFFFAOYSA-N 0.000 description 1
- JVVHLTXQSFRAFK-UHFFFAOYSA-N 2-(3-chloroanilino)-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 JVVHLTXQSFRAFK-UHFFFAOYSA-N 0.000 description 1
- UHZSWNHGVKSLGJ-UHFFFAOYSA-N 2-(3-cyanoanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCOCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(C#N)=C1 UHZSWNHGVKSLGJ-UHFFFAOYSA-N 0.000 description 1
- AGXDGYYYXSMKER-UHFFFAOYSA-N 2-(3-fluoroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=CC(F)=C1 AGXDGYYYXSMKER-UHFFFAOYSA-N 0.000 description 1
- LBMODAWYNAUDSK-UHFFFAOYSA-N 2-(3-methoxyanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound COC1=CC=CC(NC=2N=C(C(C(=O)NCC3CCOCC3)=CN=2)C(F)(F)F)=C1 LBMODAWYNAUDSK-UHFFFAOYSA-N 0.000 description 1
- KWKDTOIAEFBWCK-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCOCC2)C(C(F)(F)F)=NC=1NC1=CC=C(Br)C=C1Cl KWKDTOIAEFBWCK-UHFFFAOYSA-N 0.000 description 1
- UFSUNUOOVZESQK-UHFFFAOYSA-N 2-(4-chloro-2-fluoroanilino)-n-(cyclobutylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC(Cl)=CC=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCC1 UFSUNUOOVZESQK-UHFFFAOYSA-N 0.000 description 1
- AJPAAQCNVKLYSW-UHFFFAOYSA-N 2-(4-chloro-3-methoxyanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC(NC=2N=C(C(C(O)=O)=CN=2)C(F)(F)F)=C1 AJPAAQCNVKLYSW-UHFFFAOYSA-N 0.000 description 1
- PLUQUMDWIGIPML-UHFFFAOYSA-N 2-(4-chloro-3-methoxyanilino)-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC=2N=C(C(C(=O)NCC3CCCCC3)=CN=2)C(F)(F)F)=C1 PLUQUMDWIGIPML-UHFFFAOYSA-N 0.000 description 1
- WFLPPNWVIUGQAI-UHFFFAOYSA-N 2-(4-chloro-3-methylanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(NC=2N=C(C(C(O)=O)=CN=2)C(F)(F)F)=C1 WFLPPNWVIUGQAI-UHFFFAOYSA-N 0.000 description 1
- XZXLNMCBKSYWPI-UHFFFAOYSA-N 2-(4-cyanoanilino)-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=C(C#N)C=C1 XZXLNMCBKSYWPI-UHFFFAOYSA-N 0.000 description 1
- IJIJRQJVNRZSBI-UHFFFAOYSA-N 2-[2-methylsulfanyl-3-(trifluoromethyl)anilino]-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound C1=CC=C(C(F)(F)F)C(SC)=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCOCC1 IJIJRQJVNRZSBI-UHFFFAOYSA-N 0.000 description 1
- YKHMONCVMKIPFS-UHFFFAOYSA-N 2-[3-bromo-5-(trifluoromethyl)anilino]-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=CC(Br)=CC(NC=2N=C(C(C(=O)NCC3CCOCC3)=CN=2)C(F)(F)F)=C1 YKHMONCVMKIPFS-UHFFFAOYSA-N 0.000 description 1
- XDUSDWWYEDVOEV-UHFFFAOYSA-N 2-[3-chloro-4-(trifluoromethoxy)anilino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 XDUSDWWYEDVOEV-UHFFFAOYSA-N 0.000 description 1
- VDOBYBBKQKDUGR-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)anilino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN=C1NC1=CC=C(C(F)(F)F)C(F)=C1 VDOBYBBKQKDUGR-UHFFFAOYSA-N 0.000 description 1
- RSTJQCLUYMVEGP-UHFFFAOYSA-N 2-[4-bromo-2-(trifluoromethyl)anilino]-n-(oxan-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=CC(Br)=CC=C1NC(N=C1C(F)(F)F)=NC=C1C(=O)NCC1CCOCC1 RSTJQCLUYMVEGP-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
- XLOOIWPZXGKRNZ-UHFFFAOYSA-N 2-anilino-n-(cyclohexylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC=C1 XLOOIWPZXGKRNZ-UHFFFAOYSA-N 0.000 description 1
- MEJHQWKAUTUGKU-UHFFFAOYSA-N 2-anilino-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC=C1 MEJHQWKAUTUGKU-UHFFFAOYSA-N 0.000 description 1
- YYQGUWHFXVXQOO-GFCCVEGCSA-N 2-chloro-4-[[3-[(2R)-2-hydroxybutyl]-1-methyl-2-oxobenzimidazol-5-yl]amino]pyridine-3-carbonitrile Chemical compound ClC1=C(C#N)C(=CC=N1)NC1=CC2=C(N(C(N2C[C@@H](CC)O)=O)C)C=C1 YYQGUWHFXVXQOO-GFCCVEGCSA-N 0.000 description 1
- XGYLSRFSXKAYCR-UHFFFAOYSA-N 2-chloro-4-methylaniline Chemical compound CC1=CC=C(N)C(Cl)=C1 XGYLSRFSXKAYCR-UHFFFAOYSA-N 0.000 description 1
- VWUFOZAFKYOZJB-UHFFFAOYSA-N 2-chloro-5-fluoroaniline Chemical compound NC1=CC(F)=CC=C1Cl VWUFOZAFKYOZJB-UHFFFAOYSA-N 0.000 description 1
- GYYVHJRSLVVFQU-UHFFFAOYSA-N 2-chloro-n-(cyclopentylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)NCC1CCCC1 GYYVHJRSLVVFQU-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
- 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
- QPVGAKXHBBRRCB-UHFFFAOYSA-N 2-methylsulfanyl-3-(trifluoromethyl)aniline Chemical compound CSC1=C(N)C=CC=C1C(F)(F)F QPVGAKXHBBRRCB-UHFFFAOYSA-N 0.000 description 1
- GPWHFPWZAPOYNO-UHFFFAOYSA-N 3,3-dimethylbutan-1-amine Chemical compound CC(C)(C)CCN GPWHFPWZAPOYNO-UHFFFAOYSA-N 0.000 description 1
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 1
- HJTLKVYOWNTDPF-UHFFFAOYSA-N 3-bromo-5-(trifluoromethyl)aniline Chemical compound NC1=CC(Br)=CC(C(F)(F)F)=C1 HJTLKVYOWNTDPF-UHFFFAOYSA-N 0.000 description 1
- ZPKUUNGPBSRPRM-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C(Cl)=C1 ZPKUUNGPBSRPRM-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- VTFGJEYZCUWSAM-UHFFFAOYSA-N 3-methoxy-5-(trifluoromethyl)aniline Chemical compound COC1=CC(N)=CC(C(F)(F)F)=C1 VTFGJEYZCUWSAM-UHFFFAOYSA-N 0.000 description 1
- OQHVVOYDDRBQRI-UHFFFAOYSA-N 4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1C(F)(F)F OQHVVOYDDRBQRI-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- OREVCMGFYSUYPX-UHFFFAOYSA-N 4-amino-3-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1Cl OREVCMGFYSUYPX-UHFFFAOYSA-N 0.000 description 1
- PHXGKHTWEOPCEW-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C=C1C(F)(F)F PHXGKHTWEOPCEW-UHFFFAOYSA-N 0.000 description 1
- CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
- HIHCTGNZNHSZPP-UHFFFAOYSA-N 4-chloro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Cl HIHCTGNZNHSZPP-UHFFFAOYSA-N 0.000 description 1
- OXFYWRXLEMQSPC-UHFFFAOYSA-N 4-hydroxyoxane-4-carbonitrile Chemical compound N#CC1(O)CCOCC1 OXFYWRXLEMQSPC-UHFFFAOYSA-N 0.000 description 1
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 description 1
- LMWMDFUMJLWNLM-UHFFFAOYSA-N 6-amino-1-chlorocyclohexa-2,4-diene-1-carbonitrile Chemical compound NC1C=CC=CC1(Cl)C#N LMWMDFUMJLWNLM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 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
- 208000024827 Alzheimer disease Diseases 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
- 206010002027 Amyotrophy Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 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
- 208000027496 Behcet disease Diseases 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 102000010183 Bradykinin receptor Human genes 0.000 description 1
- 108050001736 Bradykinin receptor Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 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
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 244000089742 Citrus aurantifolia Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 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
- 241000272201 Columbiformes Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 108010037462 Cyclooxygenase 2 Proteins 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
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 1
- 208000027219 Deficiency 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
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010013980 Dyssomnias Diseases 0.000 description 1
- 206010014561 Emphysema 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
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 208000001640 Fibromyalgia Diseases 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
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 229940122165 Glycine receptor antagonist Drugs 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 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
- 101000710899 Homo sapiens Cannabinoid receptor 1 Proteins 0.000 description 1
- 101000875075 Homo sapiens Cannabinoid receptor 2 Proteins 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- 206010065952 Hyperpathia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010021135 Hypovitaminosis Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 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
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [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
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000026072 Motor neurone disease Diseases 0.000 description 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
- 206010028391 Musculoskeletal Pain Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 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
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 229910003827 NRaRb Inorganic materials 0.000 description 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 1
- 206010028836 Neck pain Diseases 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010062501 Non-cardiac chest pain Diseases 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 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
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000264897 Persea americana var. americana Species 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 208000013544 Platelet disease Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 101100391171 Schizosaccharomyces pombe (strain 972 / ATCC 24843) for3 gene Proteins 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 102000011040 TRPV Cation Channels Human genes 0.000 description 1
- 108010062740 TRPV Cation Channels Proteins 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 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
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 208000036142 Viral infection 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000009692 acute damage Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229960005305 adenosine Drugs 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
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229960002133 almotriptan Drugs 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229960000959 amineptine Drugs 0.000 description 1
- VDPUXONTAVMIKZ-UHFFFAOYSA-N amineptine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2C([NH2+]CCCCCCC(=O)O)C2=CC=CC=C21 VDPUXONTAVMIKZ-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
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000002399 aphthous stomatitis Diseases 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- XXNHMNQGAALVQM-UHFFFAOYSA-N benzyl 2-(3-chloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound N=1C=C(C(=O)OCC=2C=CC=CC=2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 XXNHMNQGAALVQM-UHFFFAOYSA-N 0.000 description 1
- RJHJVPJLOZDZSJ-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound FC(F)(F)C1=NC(Cl)=NC=C1C(=O)OCC1=CC=CC=C1 RJHJVPJLOZDZSJ-UHFFFAOYSA-N 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
- 229960003237 betaine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 208000029028 brain injury Diseases 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
- 229960001058 bupropion Drugs 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
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-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
- 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 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 210000000748 cardiovascular system Anatomy 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
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008614 cellular interaction Effects 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 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
- 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
- 229960003920 cocaine Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- GFBLFDSCAKHHGX-UHFFFAOYSA-N cyclobutanecarbonitrile Chemical compound N#CC1CCC1 GFBLFDSCAKHHGX-UHFFFAOYSA-N 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
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 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
- 229960003314 deracoxib Drugs 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
- 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
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960001259 diclofenac Drugs 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
- 230000009429 distress Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229960004242 dronabinol Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 208000024732 dysthymic disease Diseases 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
- 229940073621 enbrel Drugs 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 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
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009477 fluid bed granulation Methods 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
- 238000004108 freeze drying Methods 0.000 description 1
- 229960002284 frovatriptan Drugs 0.000 description 1
- SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-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
- 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
- 208000007565 gingivitis Diseases 0.000 description 1
- 229960002442 glucosamine Drugs 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
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229960002885 histidine Drugs 0.000 description 1
- 102000056693 human CNR2 Human genes 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
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000009610 hypersensitivity Effects 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
- 208000009326 ileitis Diseases 0.000 description 1
- 238000003384 imaging method Methods 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
- 229960004801 imipramine Drugs 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000008629 immune suppression Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 201000001881 impotence Diseases 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
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 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
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 description 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000004807 localization Effects 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
- 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
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 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
- 208000027061 mild cognitive impairment Diseases 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
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- UPGMYJPYALRFEG-UHFFFAOYSA-N n-(cyclohexylmethyl)-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NCC1CCCCC1 UPGMYJPYALRFEG-UHFFFAOYSA-N 0.000 description 1
- BQKBIQHXIFDMJB-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-(2,3-difluoroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(NC=2N=C(C(C(=O)NCC3CCCCC3)=CN=2)C(F)(F)F)=C1F BQKBIQHXIFDMJB-UHFFFAOYSA-N 0.000 description 1
- WUWMRTRVUQCLSX-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-(2,4-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCCC2)C(C(F)(F)F)=NC=1NC1=CC=C(Cl)C=C1Cl WUWMRTRVUQCLSX-UHFFFAOYSA-N 0.000 description 1
- XWKBTDCJZJBOGZ-UHFFFAOYSA-N n-(cyclopentylmethyl)-2-(2,3-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1Cl XWKBTDCJZJBOGZ-UHFFFAOYSA-N 0.000 description 1
- JJEMYLDHKIYKTA-UHFFFAOYSA-N n-(cyclopentylmethyl)-2-(3,5-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NCC2CCCC2)C(C(F)(F)F)=NC=1NC1=CC(Cl)=CC(Cl)=C1 JJEMYLDHKIYKTA-UHFFFAOYSA-N 0.000 description 1
- QFXOIUNXYAYLHC-UHFFFAOYSA-N n-(cyclopentylmethyl)-2-(3-fluoroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(NC=2N=C(C(C(=O)NCC3CCCC3)=CN=2)C(F)(F)F)=C1 QFXOIUNXYAYLHC-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- VBLNJDLBUZSLPS-UHFFFAOYSA-N n-cyclobutyl-2-(2,3-dichloroanilino)-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound N=1C=C(C(=O)NC2CCC2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1Cl VBLNJDLBUZSLPS-UHFFFAOYSA-N 0.000 description 1
- IPGJHNSSNPFECL-UHFFFAOYSA-N n-methyl-1-(oxan-4-yl)methanamine;hydrochloride Chemical compound Cl.CNCC1CCOCC1 IPGJHNSSNPFECL-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
- 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
- 230000031990 negative regulation of inflammatory response Effects 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 229960005343 ondansetron Drugs 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003349 osteoarthritic effect Effects 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
- 208000019906 panic disease Diseases 0.000 description 1
- 229960004662 parecoxib Drugs 0.000 description 1
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000004031 partial agonist Substances 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
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 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
- 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
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 239000003380 propellant Substances 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
- BLGXFZZNTVWLAY-DIRVCLHFSA-N rauwolscine 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-DIRVCLHFSA-N 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940116176 remicade Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 208000022610 schizoaffective disease 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
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000009155 sensory pathway Effects 0.000 description 1
- 239000003775 serotonin noradrenalin reuptake inhibitor 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
- 230000001568 sexual effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000004760 silicates Chemical class 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
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 210000000273 spinal nerve root Anatomy 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 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
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- SYZGVSQZONQUDV-UHFFFAOYSA-N tert-butyl n-(oxan-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCOCC1 SYZGVSQZONQUDV-UHFFFAOYSA-N 0.000 description 1
- HJGAECGPWINXCT-UHFFFAOYSA-N tert-butyl n-methyl-n-(oxan-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1CCOCC1 HJGAECGPWINXCT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- DQKVZWAEWJUKAX-UHFFFAOYSA-N thiane-4-carbonitrile Chemical compound N#CC1CCSCC1 DQKVZWAEWJUKAX-UHFFFAOYSA-N 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 208000030401 vitamin deficiency disease Diseases 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- 229960002791 zimeldine Drugs 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0219501A GB0219501D0 (en) | 2002-08-21 | 2002-08-21 | Compounds |
GB0309326A GB0309326D0 (en) | 2003-04-24 | 2003-04-24 | Compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
OA12910A true OA12910A (en) | 2006-10-13 |
Family
ID=31948030
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
OA1200500052A OA12910A (en) | 2002-08-21 | 2003-08-19 | Pyrimidine derivatives and their use as CB2 modulators. |
Country Status (35)
Country | Link |
---|---|
US (2) | US7635701B2 (fr) |
EP (2) | EP1878725B1 (fr) |
JP (1) | JP4583174B2 (fr) |
KR (1) | KR20050058367A (fr) |
CN (1) | CN100351239C (fr) |
AP (1) | AP2005003219A0 (fr) |
AR (1) | AR041016A1 (fr) |
AT (2) | ATE377591T1 (fr) |
AU (1) | AU2003264076B2 (fr) |
BR (1) | BR0313676A (fr) |
CA (1) | CA2495880C (fr) |
CY (1) | CY1107871T1 (fr) |
DE (2) | DE60335151D1 (fr) |
DK (1) | DK1539712T3 (fr) |
EA (2) | EA012703B1 (fr) |
EC (1) | ECSP055613A (fr) |
ES (1) | ES2295682T3 (fr) |
HK (1) | HK1079193A1 (fr) |
IL (2) | IL166552A0 (fr) |
IS (1) | IS7749A (fr) |
MA (1) | MA27428A1 (fr) |
MX (1) | MXPA05001960A (fr) |
MY (1) | MY137053A (fr) |
NO (1) | NO20051451L (fr) |
NZ (1) | NZ537886A (fr) |
OA (1) | OA12910A (fr) |
PE (1) | PE20040898A1 (fr) |
PL (1) | PL376047A1 (fr) |
PT (1) | PT1539712E (fr) |
SI (1) | SI1539712T1 (fr) |
TW (1) | TW200410946A (fr) |
UA (1) | UA83194C2 (fr) |
UY (1) | UY27939A1 (fr) |
WO (1) | WO2004018433A1 (fr) |
ZA (1) | ZA200500913B (fr) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
AU2003275242B2 (en) | 2002-09-27 | 2010-03-04 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
TW200505902A (en) * | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
GB0402356D0 (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 |
AU2005231507B2 (en) | 2004-04-08 | 2012-03-01 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
US7652051B2 (en) | 2004-08-25 | 2010-01-26 | Targegen, Inc. | Heterocyclic compounds and methods of use |
GB0517188D0 (en) * | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
US8604042B2 (en) | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
BR122021011787B1 (pt) | 2005-11-01 | 2022-01-25 | Impact Biomedicines, Inc | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
JP2009519349A (ja) | 2005-12-15 | 2009-05-14 | 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受容体を変調する化合物 |
US20090275611A1 (en) * | 2006-04-07 | 2009-11-05 | Boehringer Ingelheim International Gmbh | Compounds Which Modulate The CB2 Receptor |
WO2008014199A2 (fr) | 2006-07-28 | 2008-01-31 | Boehringer Ingelheim International Gmbh | Composés modulant le récepteur cb2 |
JP5159630B2 (ja) * | 2006-09-13 | 2013-03-06 | 協和発酵キリン株式会社 | 縮環複素環誘導体 |
CA2664310A1 (fr) | 2006-09-25 | 2008-04-03 | Boehringer Ingelheim International Gmbh | Composes modulant le recepteur cb2 |
KR101114704B1 (ko) * | 2006-10-04 | 2012-03-14 | 에프. 호프만-라 로슈 아게 | Cb2 수용체 조절제로서 피라진-2-카복스아마이드 유도체 |
WO2008048914A1 (fr) * | 2006-10-17 | 2008-04-24 | Boehringer Ingelheim International Gmbh | Composés qui modulent le récepteur cb2 |
US9422235B2 (en) | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
GB0705803D0 (en) * | 2007-03-28 | 2007-05-02 | Glaxo Group Ltd | Novel compounds |
EP2212694A4 (fr) * | 2007-11-06 | 2011-10-12 | Univ Emory | Procédés d'identification d'antagonistes du récepteur de nmda sûrs |
WO2009061652A1 (fr) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Composés modulant le récepteur cb2 |
US8178568B2 (en) | 2008-07-10 | 2012-05-15 | Boehringer Ingelheim International Gmbh | Sulfone compounds which modulate the CB2 receptor |
CA2737639A1 (fr) | 2008-09-25 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Composes modulant selectivement le recepteur cb2 |
TW201031650A (en) | 2008-12-02 | 2010-09-01 | Organon Nv | 1-(biphenyl-4-ylmethyl)imidazolidine-2,4-dione |
TW201031649A (en) | 2008-12-02 | 2010-09-01 | Organon Nv | 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivatives |
RU2011143740A (ru) * | 2009-03-30 | 2013-05-10 | Астеллас Фарма Инк. | Соединение пиримидина |
US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
EP2443107B1 (fr) | 2009-06-16 | 2018-08-08 | Boehringer Ingelheim International GmbH | Dérivés d'azétidine 2-carboxamide qui modulent le récepteur cb2 |
JP2013505295A (ja) | 2009-09-22 | 2013-02-14 | 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受容体を選択的に調節する化合物 |
JP2013517271A (ja) | 2010-01-15 | 2013-05-16 | 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 |
EP2542539B1 (fr) | 2010-03-05 | 2014-02-26 | Boehringer Ingelheim International GmbH | Composés tétrazoles qui modulent sélectivement le récepteur cb2 |
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 |
ES2592161T3 (es) | 2010-07-29 | 2016-11-28 | Astellas Pharma Inc. | Compuestos de piridina condensados como ligandos del receptor cannabinoide CB2 |
WO2012060847A1 (fr) | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions et procédés de traitement de la myélofibrose |
US20150261260A1 (en) * | 2013-03-15 | 2015-09-17 | Royce J. Nicholas | Method of water-proofing electronic components |
EP2803668A1 (fr) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Nouveau (cyano-dimethyl-methyl)-isoxazoles et - [1,3,4] thiadiazoles |
KR102313314B1 (ko) * | 2013-10-23 | 2021-10-19 | 아카데미아 시니카 | 신경퇴행성 질환 및 통증의 예방 및 치료에 사용하기 위한 화합물 |
MX2018012913A (es) | 2016-04-22 | 2019-01-30 | Receptor Life Sciences Inc | Compuestos medicinales y suplementos nutricionales de base vegetal de rapida accion. |
EA201892396A1 (ru) | 2016-12-02 | 2019-04-30 | Ресептор Лайф Сайенсиз, Инк. | Быстродействующие растительные лекарственные соединения и биологически активные добавки |
Family Cites Families (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5518A (en) | 1848-04-18 | Geaijst-drieb | ||
US4826689A (en) | 1984-05-21 | 1989-05-02 | University Of Rochester | Method for making uniformly sized particles from water-insoluble organic compounds |
FR2634376B1 (fr) | 1988-07-21 | 1992-04-17 | Farmalyoc | Nouvelle forme unitaire, solide et poreuse comprenant des microparticules et/ou des nanoparticules, ainsi que sa preparation |
IT1227626B (it) | 1988-11-28 | 1991-04-23 | Vectorpharma Int | Farmaci supportati aventi velocita' di dissoluzione aumentata e procedimento per la loro preparazione |
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 |
IT1243390B (it) | 1990-11-22 | 1994-06-10 | Vectorpharma Int | Composizioni farmaceutiche in forma di particelle atte al rilascio controllato di sostanze farmacologicamente attive e procedimento per la loro preparazione. |
US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
US5552160A (en) | 1991-01-25 | 1996-09-03 | Nanosystems L.L.C. | Surface modified NSAID nanoparticles |
HUT63941A (en) * | 1992-05-15 | 1993-11-29 | Hoechst Ag | Process for producing 4-alkyl-substituted pyrimidine-5-carboxanilide derivatives, and fungicidal compositions comprising same |
HUT70952A (en) | 1992-06-10 | 1995-11-28 | Eastman Kodak Co | Surface modified nanoparticles based on nosteroidal inflammatory drugs, process for preparing them and pharmaceutical compns. contg. them |
FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
US5298262A (en) | 1992-12-04 | 1994-03-29 | Sterling Winthrop Inc. | Use of ionic cloud point modifiers to prevent particle aggregation during sterilization |
US5346702A (en) | 1992-12-04 | 1994-09-13 | Sterling Winthrop Inc. | Use of non-ionic cloud point modifiers to minimize nanoparticle aggregation during sterilization |
US5302401A (en) | 1992-12-09 | 1994-04-12 | Sterling Winthrop Inc. | Method to reduce particle size growth during lyophilization |
US5340564A (en) | 1992-12-10 | 1994-08-23 | Sterling Winthrop Inc. | Formulations comprising olin 10-G to prevent particle aggregation and increase stability |
US5336507A (en) | 1992-12-11 | 1994-08-09 | Sterling Winthrop Inc. | Use of charged phospholipids to reduce nanoparticle aggregation |
US5429824A (en) | 1992-12-15 | 1995-07-04 | Eastman Kodak Company | Use of tyloxapole as a nanoparticle stabilizer and dispersant |
US5352459A (en) | 1992-12-16 | 1994-10-04 | Sterling Winthrop Inc. | Use of purified surface modifiers to prevent particle aggregation during sterilization |
US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
CZ101496A3 (en) | 1993-10-12 | 1996-11-13 | Du Pont Merck Pharma | N-alkyl-n-aryl-pyrimidinamines and derivatives thereof |
US5466823A (en) | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
US5587143A (en) | 1994-06-28 | 1996-12-24 | Nanosystems L.L.C. | Butylene oxide-ethylene oxide block copolymer surfactants as stabilizer coatings for nanoparticle compositions |
US5585108A (en) | 1994-12-30 | 1996-12-17 | Nanosystems L.L.C. | Formulations of oral gastrointestinal therapeutic agents in combination with pharmaceutically acceptable clays |
US5665331A (en) | 1995-01-10 | 1997-09-09 | Nanosystems L.L.C. | Co-microprecipitation of nanoparticulate pharmaceutical agents with crystal growth modifiers |
US5560932A (en) | 1995-01-10 | 1996-10-01 | Nano Systems L.L.C. | Microprecipitation of nanoparticulate pharmaceutical agents |
US5662883A (en) | 1995-01-10 | 1997-09-02 | Nanosystems L.L.C. | Microprecipitation of micro-nanoparticulate pharmaceutical agents |
US5571536A (en) | 1995-02-06 | 1996-11-05 | Nano Systems L.L.C. | Formulations of compounds as nanoparticulate dispersions in digestible oils or fatty acids |
US5560931A (en) | 1995-02-14 | 1996-10-01 | Nawosystems L.L.C. | Formulations of compounds as nanoparticulate dispersions in digestible oils or fatty acids |
US5503723A (en) | 1995-02-08 | 1996-04-02 | Eastman Kodak Company | Isolation of ultra small particles |
US5622938A (en) | 1995-02-09 | 1997-04-22 | Nano Systems L.L.C. | Sugar base surfactant for nanocrystals |
US5518738A (en) | 1995-02-09 | 1996-05-21 | Nanosystem L.L.C. | Nanoparticulate nsaid compositions |
US5534270A (en) | 1995-02-09 | 1996-07-09 | Nanosystems Llc | Method of preparing stable drug nanoparticles |
US5591456A (en) | 1995-02-10 | 1997-01-07 | Nanosystems L.L.C. | Milled naproxen with hydroxypropyl cellulose as a dispersion stabilizer |
US5633272A (en) | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
AU699593B2 (en) | 1995-02-13 | 1998-12-10 | G.D. Searle & Co. | Substituted isoxazoles for the treatment of inflammation |
US5573783A (en) | 1995-02-13 | 1996-11-12 | Nano Systems L.L.C. | Redispersible nanoparticulate film matrices with protective overcoats |
US5510118A (en) | 1995-02-14 | 1996-04-23 | Nanosystems Llc | Process for preparing therapeutic compositions containing nanoparticles |
US5580579A (en) | 1995-02-15 | 1996-12-03 | Nano Systems L.L.C. | Site-specific adhesion within the GI tract using nanoparticles stabilized by high molecular weight, linear poly (ethylene oxide) polymers |
US5747001A (en) | 1995-02-24 | 1998-05-05 | Nanosystems, L.L.C. | Aerosols containing beclomethazone nanoparticle dispersions |
US5718919A (en) | 1995-02-24 | 1998-02-17 | Nanosystems L.L.C. | Nanoparticles containing the R(-)enantiomer of ibuprofen |
US5565188A (en) | 1995-02-24 | 1996-10-15 | Nanosystems L.L.C. | Polyalkylene block copolymers as surface modifiers for nanoparticles |
US5811428A (en) * | 1995-12-18 | 1998-09-22 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
EP0850228A1 (fr) | 1995-09-01 | 1998-07-01 | Signal Pharmaceuticals, Inc. | Carboxamides de pyrimidine et composes associes, et methodes de traitement d'etats inflammatoires |
UA57002C2 (uk) | 1995-10-13 | 2003-06-16 | Мерк Фросст Кенада Енд Ко./Мерк Фросст Кенада Енд Сі. | Похідне (метилсульфоніл)феніл-2-(5н)-фуранону, фармацевтична композиція та спосіб лікування |
WO1997014407A1 (fr) | 1995-10-17 | 1997-04-24 | Research Triangle Pharmaceuticals | Administration de medicaments insolubles |
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 |
EP1288206B1 (fr) | 1996-04-12 | 2008-09-17 | G.D. Searle LLC | Dérivés de benzène-sulphonamide substitués en tant que précurseurs des inhibiteurs du COX-2 |
IL127441A (en) | 1996-07-18 | 2003-02-12 | Merck Frosst Canada Inc | Substituted pyridines, pharmaceutical compositions comprising them and their use in the preparation of anti-inflammatory medicaments or as selective cyclooxygenase-2 inhibitors |
WO1998035666A1 (fr) | 1997-02-13 | 1998-08-20 | Nanosystems Llc | Preparation de pastilles de naproxene nanoparticulaire |
CO4960662A1 (es) | 1997-08-28 | 2000-09-25 | Novartis Ag | Ciertos acidos 5-alquil-2-arilaminofenilaceticos y sus derivados |
CN1155600C (zh) | 1997-09-05 | 2004-06-30 | 葛兰素集团有限公司 | 2,3-二芳基吡唑并[1,5-b]哒嗪衍生物,其制备方法和用作环氧酶2抑制剂 |
US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
ES2194477T3 (es) | 1998-06-19 | 2003-11-16 | Skyepharma Canada Inc | Procedimiento para generar particulas de compuestos insolubles en agua con un tamaño de hasta 2000 nm. |
EP1117384A1 (fr) | 1998-10-01 | 2001-07-25 | Elan Pharma International Limited | Liberation regulee de compositions nanoparticulaires |
WO2000026216A1 (fr) | 1998-11-03 | 2000-05-11 | Glaxo Group Limited | Derives de pyrazolopyridine utilises comme inhibiteurs selectifs de cox-2 |
US6180136B1 (en) | 1998-11-10 | 2001-01-30 | Idexx Laboratories, Inc. | Phospholipid-coated microcrystals for the sustained release of pharmacologically active compounds and methods of their manufacture and use |
EP1133280A1 (fr) | 1998-11-20 | 2001-09-19 | RTP Pharma Inc. | Procede de preparation de suspensions stables de microparticules insolubles |
US6025683A (en) | 1998-12-23 | 2000-02-15 | Stryker Corporation | Motor control circuit for regulating a D.C. motor |
GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
JP2002538157A (ja) | 1999-02-27 | 2002-11-12 | グラクソ グループ リミテッド | ピラゾロピリジン |
GB9927844D0 (en) * | 1999-11-26 | 2000-01-26 | Glaxo Group Ltd | Chemical compounds |
ES2236007T3 (es) | 1999-12-08 | 2005-07-16 | Pharmacia Corporation | Composiciones de inhibidor de ciclooxigenasa-2 ue tiene un efecto terapeutico rapido. |
GB0003224D0 (en) * | 2000-02-11 | 2000-04-05 | Glaxo Group Ltd | Chemical compounds |
HU230396B1 (hu) | 2000-06-28 | 2016-04-28 | Smithkline Beecham Plc | Nedves őrlési eljárás |
GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
KR100571339B1 (ko) | 2000-08-31 | 2006-04-17 | 에프. 호프만-라 로슈 아게 | 세포증식 억제제로서의 7-옥소 피리도피리미딘 |
GB0021494D0 (en) | 2000-09-01 | 2000-10-18 | Glaxo Group Ltd | Chemical comkpounds |
WO2002060447A1 (fr) | 2001-01-29 | 2002-08-08 | University Of Connecticut | Aminoalkylindoles cannabimimetiques selectifs d'un recepteur |
US7507767B2 (en) | 2001-02-08 | 2009-03-24 | Schering Corporation | Cannabinoid receptor ligands |
WO2002066036A1 (fr) | 2001-02-20 | 2002-08-29 | Bristol-Myers Squibb Company | Derives de 2,4-disubstitue pyrimidine-5-carboxamide en tant que modulateur des canaux potassium kcnq |
FR2839718B1 (fr) | 2002-05-17 | 2004-06-25 | Sanofi Synthelabo | Derives d'indole, leur procede de preparation et les compositions pharmaceutiques en contenant |
AU2003243637A1 (en) | 2002-06-19 | 2004-01-06 | Schering Corporation | Cannabinoid receptor agonists |
US7449456B2 (en) | 2002-06-28 | 2008-11-11 | Astellas Pharma, Inc. | Diaminopyrimidinecarboxamide derivative |
UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
AU2003260436A1 (en) | 2002-08-21 | 2004-03-11 | Glaxo Group Limited | Pyrimidine compounds |
AU2003275242B2 (en) | 2002-09-27 | 2010-03-04 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
GB0222493D0 (en) | 2002-09-27 | 2002-11-06 | Glaxo Group Ltd | Compounds |
GB0222495D0 (en) | 2002-09-27 | 2002-11-06 | Glaxo Group Ltd | Compounds |
TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
-
2003
- 2003-08-14 UY UY27939A patent/UY27939A1/es not_active Application Discontinuation
- 2003-08-19 PE PE2003000839A patent/PE20040898A1/es not_active Application Discontinuation
- 2003-08-19 CN CNB038241293A patent/CN100351239C/zh not_active Expired - Fee Related
- 2003-08-19 NZ NZ537886A patent/NZ537886A/en unknown
- 2003-08-19 EA EA200700934A patent/EA012703B1/ru not_active IP Right Cessation
- 2003-08-19 OA OA1200500052A patent/OA12910A/en unknown
- 2003-08-19 AU AU2003264076A patent/AU2003264076B2/en not_active Ceased
- 2003-08-19 EP EP07119063A patent/EP1878725B1/fr not_active Expired - Lifetime
- 2003-08-19 ES ES03792388T patent/ES2295682T3/es not_active Expired - Lifetime
- 2003-08-19 AP AP2005003219A patent/AP2005003219A0/xx unknown
- 2003-08-19 DK DK03792388T patent/DK1539712T3/da active
- 2003-08-19 TW TW092122692A patent/TW200410946A/zh unknown
- 2003-08-19 EP EP03792388A patent/EP1539712B1/fr not_active Expired - Lifetime
- 2003-08-19 EA EA200500392A patent/EA010130B1/ru not_active IP Right Cessation
- 2003-08-19 MX MXPA05001960A patent/MXPA05001960A/es active IP Right Grant
- 2003-08-19 BR BR0313676-0A patent/BR0313676A/pt not_active IP Right Cessation
- 2003-08-19 PT PT03792388T patent/PT1539712E/pt unknown
- 2003-08-19 DE DE60335151T patent/DE60335151D1/de not_active Expired - Lifetime
- 2003-08-19 AT AT03792388T patent/ATE377591T1/de active
- 2003-08-19 US US10/524,470 patent/US7635701B2/en not_active Expired - Fee Related
- 2003-08-19 JP JP2004530220A patent/JP4583174B2/ja not_active Expired - Fee Related
- 2003-08-19 AT AT07119063T patent/ATE489369T1/de not_active IP Right Cessation
- 2003-08-19 CA CA2495880A patent/CA2495880C/fr not_active Expired - Fee Related
- 2003-08-19 PL PL03376047A patent/PL376047A1/xx not_active Application Discontinuation
- 2003-08-19 KR KR1020057002813A patent/KR20050058367A/ko not_active Application Discontinuation
- 2003-08-19 DE DE60317348T patent/DE60317348T2/de not_active Expired - Lifetime
- 2003-08-19 WO PCT/EP2003/009217 patent/WO2004018433A1/fr active IP Right Grant
- 2003-08-19 SI SI200331088T patent/SI1539712T1/sl unknown
- 2003-08-19 MY MYPI20033143A patent/MY137053A/en unknown
- 2003-08-19 UA UAA200501583A patent/UA83194C2/ru unknown
- 2003-08-19 AR ARP030102997A patent/AR041016A1/es unknown
-
2005
- 2005-01-27 IL IL16655205A patent/IL166552A0/xx unknown
- 2005-02-01 ZA ZA200500913A patent/ZA200500913B/xx unknown
- 2005-02-18 EC EC2005005613A patent/ECSP055613A/es unknown
- 2005-03-07 MA MA28132A patent/MA27428A1/fr unknown
- 2005-03-17 IS IS7749A patent/IS7749A/is unknown
- 2005-03-18 NO NO20051451A patent/NO20051451L/no not_active Application Discontinuation
- 2005-11-29 HK HK05110876A patent/HK1079193A1/xx not_active IP Right Cessation
-
2007
- 2007-08-27 IL IL185549A patent/IL185549A0/en unknown
-
2008
- 2008-01-31 CY CY20081100115T patent/CY1107871T1/el unknown
-
2009
- 2009-10-21 US US12/582,861 patent/US20100041654A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
OA12910A (en) | Pyrimidine derivatives and their use as CB2 modulators. | |
US7589206B2 (en) | Pyrrolopyridine derivatives | |
US20080280952A1 (en) | Pyridine Derivatives as Connabinoid Receptor Modulators | |
EP1565442B1 (fr) | Derives de pyridine modulateurs du recepteur cb2 | |
EP1534687B1 (fr) | Derives de 2-phenylamino-4-trifluoromethyl-5-(benzyl- ou pyridin-4-ylmethyl)carbamoylpyrimidine comme modulateurs selectifs du recepteur cannabinoide cb2 | |
US20080261977A1 (en) | Pyrimidine Derivatives as Cannabinoid Receptor Modulators | |
WO2005074939A1 (fr) | Combinaison de modulateurs du cb2 et d'inhibiteurs de la pde4 utilisee en medecine | |
US20090264452A1 (en) | 2-(Phenylamino)-Pyrimidin-5-Amides As Cannabinoid 2 Receptors Modulators for the Treatment of Immune or Inflammatory Disorders | |
EP1809611A1 (fr) | Composes a base de pyrimidinone inversee servant de calcilytiques | |
US20080221097A1 (en) | Imidazopyridine Derivatives as Cannabinoid Receptor Ligands | |
EP1979358A1 (fr) | Composes | |
AU2007211954A1 (en) | Pyrimidine derivatives and their use as CB2 modulators |