MXPA05006728A - Amidas sustituidas. - Google Patents
Amidas sustituidas.Info
- Publication number
- MXPA05006728A MXPA05006728A MXPA05006728A MXPA05006728A MXPA05006728A MX PA05006728 A MXPA05006728 A MX PA05006728A MX PA05006728 A MXPA05006728 A MX PA05006728A MX PA05006728 A MXPA05006728 A MX PA05006728A MX PA05006728 A MXPA05006728 A MX PA05006728A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- methyl
- pharmaceutically acceptable
- aryl
- propyl
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 239
- 238000011282 treatment Methods 0.000 claims abstract description 96
- 208000008589 Obesity Diseases 0.000 claims abstract description 54
- 235000020824 obesity Nutrition 0.000 claims abstract description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
- 230000002265 prevention Effects 0.000 claims abstract description 37
- 239000003814 drug Substances 0.000 claims abstract description 28
- 208000035475 disorder Diseases 0.000 claims abstract description 22
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 229940079593 drug Drugs 0.000 claims abstract description 21
- 206010010774 Constipation Diseases 0.000 claims abstract description 14
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 14
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 13
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 208000030814 Eating disease Diseases 0.000 claims abstract description 11
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 11
- 208000006673 asthma Diseases 0.000 claims abstract description 10
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 claims abstract description 10
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 9
- 201000009032 substance abuse Diseases 0.000 claims abstract description 9
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 9
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 231100000736 substance abuse Toxicity 0.000 claims abstract description 7
- 208000026139 Memory disease Diseases 0.000 claims abstract description 6
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 206010027599 migraine Diseases 0.000 claims abstract description 6
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims abstract description 5
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 5
- 206010015037 epilepsy Diseases 0.000 claims abstract description 5
- 201000001119 neuropathy Diseases 0.000 claims abstract description 5
- 230000007823 neuropathy Effects 0.000 claims abstract description 5
- 208000033808 peripheral neuropathy Diseases 0.000 claims abstract description 5
- 230000002792 vascular Effects 0.000 claims abstract description 5
- -1 cycloheteroalkyl Chemical group 0.000 claims description 148
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 25
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 235000012631 food intake Nutrition 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 230000037406 food intake Effects 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 208000010235 Food Addiction Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims 1
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 abstract description 49
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 abstract description 49
- 239000005557 antagonist Substances 0.000 abstract description 26
- 239000000556 agonist Substances 0.000 abstract description 23
- 102000005962 receptors Human genes 0.000 abstract description 19
- 108020003175 receptors Proteins 0.000 abstract description 19
- 230000002757 inflammatory effect Effects 0.000 abstract description 5
- 230000001629 suppression Effects 0.000 abstract description 5
- 206010014612 Encephalitis viral Diseases 0.000 abstract description 4
- 206010016654 Fibrosis Diseases 0.000 abstract description 4
- 201000006417 multiple sclerosis Diseases 0.000 abstract description 4
- 201000002498 viral encephalitis Diseases 0.000 abstract description 4
- 208000035895 Guillain-Barré syndrome Diseases 0.000 abstract description 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 abstract description 3
- 208000016285 Movement disease Diseases 0.000 abstract description 3
- 230000002490 cerebral effect Effects 0.000 abstract description 3
- 210000004185 liver Anatomy 0.000 abstract description 2
- 206010019196 Head injury Diseases 0.000 abstract 1
- 230000007882 cirrhosis Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 148
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 111
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 88
- 238000000034 method Methods 0.000 description 74
- 238000005481 NMR spectroscopy Methods 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000003756 stirring Methods 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 229940075993 receptor modulator Drugs 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 239000000164 antipsychotic agent Substances 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- 239000012267 brine Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000037396 body weight Effects 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 12
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 9
- 108050007331 Cannabinoid receptor Proteins 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- SZFUWUOHDRMCKD-UHFFFAOYSA-N 5-chloro-1h-pyridin-2-one Chemical compound OC1=CC=C(Cl)C=N1 SZFUWUOHDRMCKD-UHFFFAOYSA-N 0.000 description 8
- 244000025254 Cannabis sativa Species 0.000 description 8
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 description 8
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 8
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 8
- 206010026749 Mania Diseases 0.000 description 8
- 230000001976 improved effect Effects 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 7
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 6
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 6
- 108090001061 Insulin Proteins 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000000924 antiasthmatic agent Substances 0.000 description 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical group CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Chemical class 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 description 6
- 229960002715 nicotine Drugs 0.000 description 6
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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| ES2294330T3 (es) | 2002-08-02 | 2008-04-01 | MERCK & CO., INC. | Derivados de furo(2,3-b)piridina sustituidos. |
| AU2003300967B2 (en) | 2002-12-19 | 2009-05-28 | Merck Sharp & Dohme Corp. | Substituted amides |
| US7754188B2 (en) | 2003-06-30 | 2010-07-13 | Merck Sharp & Dohme Corp. | Radiolabeled cannabinoid-1 receptor modulators |
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| US7880001B2 (en) * | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| US8198331B2 (en) | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| ATE555081T1 (de) * | 2005-01-05 | 2012-05-15 | Abbott Lab | Adamantyl-derivate als inhibitoren des 11-beta- hydroxysteroid-dehydrogenase-1-enzyms |
| US20090192198A1 (en) | 2005-01-05 | 2009-07-30 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| CN102816081A (zh) * | 2005-01-05 | 2012-12-12 | 雅培制药有限公司 | 11-β-羟甾类脱氢酶1型酶的抑制剂 |
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| KR20080027908A (ko) | 2005-06-30 | 2008-03-28 | 프로시디온 리미티드 | Ｇｐｃｒ 효능제 |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| SI2114933T1 (sl) | 2007-01-04 | 2012-01-31 | Prosidion Ltd Windrush Court | Piperidinski gpcr-agonisti |
| AR064736A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| AR064735A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr y composicion farmaceutica en base al compuesto |
| JP2010514832A (ja) | 2007-01-04 | 2010-05-06 | プロシディオン・リミテッド | ピペリジンｇｐｃｒアゴニスト |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP5736098B2 (ja) * | 2007-08-21 | 2015-06-17 | アッヴィ・インコーポレイテッド | 中枢神経系障害を治療するための医薬組成物 |
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| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120050A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| JPH07173120A (ja) * | 1993-10-08 | 1995-07-11 | Banyu Pharmaceut Co Ltd | 置換芳香族カルボン酸誘導体 |
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| AR045533A1 (es) | 2003-09-02 | 2005-11-02 | Solvay Pharm Gmbh | Uso de un compuesto antagonista de receptor de cb1, composicion farmaceutica y metodo de tratamiento y/o profilaxis de enfermedades relacionadas con dicho receptor de cb1 |
| EP1663215A1 (en) | 2003-09-02 | 2006-06-07 | Solvay Pharmaceuticals GmbH | Novel medical use of selective cb1- receptor antagonists |
| EP1663113A4 (en) | 2003-09-18 | 2007-06-13 | Merck & Co Inc | SUBSTITUTED SULFONAMIDE |
| RU2006117627A (ru) | 2003-10-24 | 2007-12-10 | Зольвай Фармасьютиклз Гмбх (De) | Новые применения в медицине соединений, обладающих антагонистической активностью по отношению к св1, и комбинированное лечение с применением этих соединений |
| US8166053B2 (en) | 2003-10-30 | 2012-04-24 | Ntt Docomo, Inc. | Method and apparatus for schema-driven XML parsing optimization |
-
2003
- 2003-12-15 AU AU2003300967A patent/AU2003300967B2/en not_active Ceased
- 2003-12-15 EP EP03814048A patent/EP1575901B1/en not_active Expired - Lifetime
- 2003-12-15 US US10/538,395 patent/US7348456B2/en not_active Expired - Fee Related
- 2003-12-15 JP JP2004563615A patent/JP4719469B2/ja not_active Expired - Fee Related
- 2003-12-15 MX MXPA05006728A patent/MXPA05006728A/es active IP Right Grant
- 2003-12-15 CA CA2510785A patent/CA2510785C/en not_active Expired - Fee Related
- 2003-12-15 KR KR1020057011407A patent/KR20050088194A/ko not_active Ceased
- 2003-12-15 CN CNA2003801097502A patent/CN1747926A/zh active Pending
- 2003-12-15 WO PCT/US2003/040040 patent/WO2004058145A2/en not_active Ceased
-
2008
- 2008-01-14 US US12/008,728 patent/US7576239B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050088194A (ko) | 2005-09-02 |
| US7576239B2 (en) | 2009-08-18 |
| CN1747926A (zh) | 2006-03-15 |
| US20060106071A1 (en) | 2006-05-18 |
| US7348456B2 (en) | 2008-03-25 |
| CA2510785A1 (en) | 2004-07-15 |
| WO2004058145A3 (en) | 2004-09-02 |
| US20080194645A1 (en) | 2008-08-14 |
| EP1575901A2 (en) | 2005-09-21 |
| AU2003300967A1 (en) | 2004-07-22 |
| EP1575901A4 (en) | 2009-03-18 |
| JP2006510716A (ja) | 2006-03-30 |
| CA2510785C (en) | 2013-04-09 |
| JP4719469B2 (ja) | 2011-07-06 |
| EP1575901B1 (en) | 2012-10-10 |
| WO2004058145A2 (en) | 2004-07-15 |
| AU2003300967B2 (en) | 2009-05-28 |
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