IL195632A - Preserved carboxamides, pharmaceuticals containing them and their use in the preparation of pain medication - Google Patents
Preserved carboxamides, pharmaceuticals containing them and their use in the preparation of pain medicationInfo
- Publication number
- IL195632A IL195632A IL195632A IL19563208A IL195632A IL 195632 A IL195632 A IL 195632A IL 195632 A IL195632 A IL 195632A IL 19563208 A IL19563208 A IL 19563208A IL 195632 A IL195632 A IL 195632A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- preparation
- mmol
- phenyl
- Prior art date
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 44
- -1 carboxamide compounds Chemical class 0.000 title claims abstract description 35
- 230000036407 pain Effects 0.000 title claims abstract description 34
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 8
- 239000003814 drug Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 78
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- LXZFJIRPRVGCDF-PRHODGIISA-N (1r,2r)-n-[3-(4-chlorophenyl)-4-methyl-1,2-thiazol-5-yl]-2-methylcyclopropane-1-carboxamide Chemical compound C[C@@H]1C[C@H]1C(=O)NC1=C(C)C(C=2C=CC(Cl)=CC=2)=NS1 LXZFJIRPRVGCDF-PRHODGIISA-N 0.000 claims description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
- 238000000034 method Methods 0.000 description 52
- 239000000243 solution Substances 0.000 description 46
- 238000003756 stirring Methods 0.000 description 38
- 239000000203 mixture Substances 0.000 description 36
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- 102000005962 receptors Human genes 0.000 description 21
- 108020003175 receptors Proteins 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 230000001684 chronic effect Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- 208000000094 Chronic Pain Diseases 0.000 description 10
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 description 9
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 description 9
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 9
- 230000002757 inflammatory effect Effects 0.000 description 9
- 208000004296 neuralgia Diseases 0.000 description 9
- 208000021722 neuropathic pain Diseases 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 235000015320 potassium carbonate Nutrition 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- UEGDTXGDZZESGT-MWLCHTKSSA-N benzyl (1r,2r)-2-methylcyclopropane-1-carboxylate Chemical compound C[C@@H]1C[C@H]1C(=O)OCC1=CC=CC=C1 UEGDTXGDZZESGT-MWLCHTKSSA-N 0.000 description 6
- 150000003857 carboxamides Chemical group 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 125000002346 iodo group Chemical group I* 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- MBRXSOUHUFBPQC-RFPWEZLHSA-N (6s,8s,9r,10s,11s,13s,14s,16r,17s)-9-chloro-6,11-difluoro-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1F MBRXSOUHUFBPQC-RFPWEZLHSA-N 0.000 description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000006399 behavior Effects 0.000 description 5
- 229960002504 capsaicin Drugs 0.000 description 5
- 235000017663 capsaicin Nutrition 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 229930195712 glutamate Natural products 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 230000002085 persistent effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 210000001032 spinal nerve Anatomy 0.000 description 5
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 5
- AYEGPMGNMOIHDL-QWWZWVQMSA-N (1r,2r)-2-methylcyclopropane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H]1C(O)=O AYEGPMGNMOIHDL-QWWZWVQMSA-N 0.000 description 4
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 4
- 208000004454 Hyperalgesia Diseases 0.000 description 4
- STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000005356 chiral GC Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 206010015037 epilepsy Diseases 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003040 nociceptive effect Effects 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
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- VCSKFTJGUYAXOC-CHDUMGHJSA-N (2s)-2-amino-3-phenylpropan-1-ol;(1r,2r)-2-methylcyclopropane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H]1C(O)=O.OC[C@@H](N)CC1=CC=CC=C1 VCSKFTJGUYAXOC-CHDUMGHJSA-N 0.000 description 3
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- VAIJKTHAHKDKKB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-methyl-1,2-thiazol-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NSC(N)=C1C VAIJKTHAHKDKKB-UHFFFAOYSA-N 0.000 description 3
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- 239000005909 Kieselgur Substances 0.000 description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 102000030621 adenylate cyclase Human genes 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 238000005452 bending Methods 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
- 239000012455 biphasic mixture Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 206010008118 cerebral infarction Diseases 0.000 description 2
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- BSEXNZMHLUMQKR-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1.NC(=O)C1CC1 BSEXNZMHLUMQKR-UHFFFAOYSA-N 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81183906P | 2006-06-08 | 2006-06-08 | |
| PCT/US2007/070572 WO2008103185A2 (en) | 2006-06-08 | 2007-06-07 | Substituted carboxamides as group i metabotropic receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL195632A0 IL195632A0 (en) | 2009-09-01 |
| IL195632A true IL195632A (en) | 2013-11-28 |
Family
ID=39673278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL195632A IL195632A (en) | 2006-06-08 | 2008-12-01 | Preserved carboxamides, pharmaceuticals containing them and their use in the preparation of pain medication |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US7960419B2 (enExample) |
| EP (1) | EP2076502B1 (enExample) |
| JP (1) | JP5108878B2 (enExample) |
| KR (1) | KR101051559B1 (enExample) |
| CN (1) | CN101466691B (enExample) |
| AT (1) | ATE509921T1 (enExample) |
| AU (1) | AU2007347428B2 (enExample) |
| BR (1) | BRPI0712862A2 (enExample) |
| CA (1) | CA2652074C (enExample) |
| CR (1) | CR10410A (enExample) |
| CY (1) | CY1111588T1 (enExample) |
| DK (1) | DK2076502T3 (enExample) |
| EA (1) | EA014233B1 (enExample) |
| EC (1) | ECSP088939A (enExample) |
| ES (1) | ES2362949T3 (enExample) |
| HR (1) | HRP20110436T1 (enExample) |
| IL (1) | IL195632A (enExample) |
| MA (1) | MA30620B1 (enExample) |
| MX (1) | MX2008015485A (enExample) |
| MY (1) | MY148084A (enExample) |
| NO (1) | NO341474B1 (enExample) |
| NZ (1) | NZ573352A (enExample) |
| PL (1) | PL2076502T3 (enExample) |
| PT (1) | PT2076502E (enExample) |
| RS (1) | RS51818B (enExample) |
| SI (1) | SI2076502T1 (enExample) |
| TN (1) | TNSN08506A1 (enExample) |
| UA (1) | UA95480C2 (enExample) |
| WO (1) | WO2008103185A2 (enExample) |
| ZA (1) | ZA200809111B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0804685D0 (en) | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| MX2010010781A (es) | 2008-04-04 | 2010-12-14 | Lilly Co Eli | 3-indazolil-4-piridilisotiazoles. |
| EP2443113A1 (en) * | 2009-06-15 | 2012-04-25 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| JP5779181B2 (ja) | 2009-09-16 | 2015-09-16 | ザ ユニバーシティ オブ エディンバラ | （４−フェニル−ピペリジン−１−イル）−［５−（１ｈ−ピラゾール−４−イル）−チオフェン−３−イル］−メタノン化合物及びそれらの使用 |
| EP2563780B1 (en) | 2010-04-29 | 2015-05-06 | The University Of Edinburgh | 3,3-disubstituted-(8-aza-bicyclo[3.2.1]oct-8-yl)-[5-(1h-pyrazol-4-yl)-thiophen-3-yl]-methanones as inhibitors of 11(beta)-hsd1 |
| DK2921489T3 (en) | 2012-11-13 | 2017-10-16 | Nissan Chemical Ind Ltd | 2-pyridone-RELATED |
| AU2017329677A1 (en) | 2016-09-23 | 2019-04-18 | Bayer Aktiengesellschaft | N 3 -cyclically substituted thienouraciles and use thereof |
| CN117567266B (zh) * | 2023-11-07 | 2024-06-14 | 康龙化成手性医药技术(宁波)有限公司 | 一种制备2-甲基环丙羧酸的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL72091A0 (en) | 1983-06-20 | 1984-10-31 | Lilly Co Eli | N'-substituted(3-aryl 5-isothiazolyl)urea derivatives |
| DE4328425A1 (de) | 1993-08-24 | 1995-03-02 | Basf Ag | Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung |
| DK124393D0 (da) | 1993-11-03 | 1993-11-03 | Lundbeck & Co As H | Compounds |
| DE19542372A1 (de) * | 1995-11-14 | 1997-05-15 | Bayer Ag | Acylierte 5-Aminoisothiazole |
| UA60365C2 (uk) * | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| JP3411262B2 (ja) * | 1999-08-20 | 2003-05-26 | 萬有製薬株式会社 | 新規スピロ化合物 |
| JP2005501073A (ja) * | 2001-08-06 | 2005-01-13 | フアルマシア・イタリア・エツセ・ピー・アー | キナーゼ阻害薬活性を有するアミノイソオキサゾール誘導体 |
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
| WO2005113534A2 (en) * | 2004-05-12 | 2005-12-01 | Schering Corporation | Cxcr1 and cxcr2 chemokine antagonists |
| BRPI0515571A (pt) * | 2004-09-23 | 2008-07-29 | Pfizer Prod Inc | agonistas de receptor de trombopoetina |
-
2007
- 2007-06-07 PL PL07873705T patent/PL2076502T3/pl unknown
- 2007-06-07 SI SI200730695T patent/SI2076502T1/sl unknown
- 2007-06-07 DK DK07873705.3T patent/DK2076502T3/da active
- 2007-06-07 NZ NZ573352A patent/NZ573352A/en not_active IP Right Cessation
- 2007-06-07 EP EP07873705A patent/EP2076502B1/en active Active
- 2007-06-07 HR HR20110436T patent/HRP20110436T1/hr unknown
- 2007-06-07 KR KR1020087029772A patent/KR101051559B1/ko not_active Expired - Fee Related
- 2007-06-07 MX MX2008015485A patent/MX2008015485A/es active IP Right Grant
- 2007-06-07 JP JP2009514523A patent/JP5108878B2/ja not_active Expired - Fee Related
- 2007-06-07 ES ES07873705T patent/ES2362949T3/es active Active
- 2007-06-07 UA UAA200813907A patent/UA95480C2/uk unknown
- 2007-06-07 AU AU2007347428A patent/AU2007347428B2/en not_active Ceased
- 2007-06-07 RS RS20110336A patent/RS51818B/sr unknown
- 2007-06-07 US US12/300,415 patent/US7960419B2/en active Active
- 2007-06-07 PT PT07873705T patent/PT2076502E/pt unknown
- 2007-06-07 CA CA2652074A patent/CA2652074C/en not_active Expired - Fee Related
- 2007-06-07 AT AT07873705T patent/ATE509921T1/de active
- 2007-06-07 EA EA200870516A patent/EA014233B1/ru not_active IP Right Cessation
- 2007-06-07 CN CN2007800211890A patent/CN101466691B/zh not_active Expired - Fee Related
- 2007-06-07 BR BRPI0712862-2A patent/BRPI0712862A2/pt not_active IP Right Cessation
- 2007-06-07 WO PCT/US2007/070572 patent/WO2008103185A2/en not_active Ceased
- 2007-06-07 MY MYPI20084973A patent/MY148084A/en unknown
- 2007-10-29 CR CR10410A patent/CR10410A/es unknown
-
2008
- 2008-10-23 ZA ZA200809111A patent/ZA200809111B/xx unknown
- 2008-12-01 IL IL195632A patent/IL195632A/en not_active IP Right Cessation
- 2008-12-02 NO NO20085028A patent/NO341474B1/no not_active IP Right Cessation
- 2008-12-03 EC EC2008008939A patent/ECSP088939A/es unknown
- 2008-12-05 TN TNP2008000506A patent/TNSN08506A1/en unknown
-
2009
- 2009-01-06 MA MA31553A patent/MA30620B1/fr unknown
-
2011
- 2011-06-24 CY CY20111100600T patent/CY1111588T1/el unknown
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