NZ571142A - Synthesis of acylaminoalkenylene amides such as (4R)-4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-4(-3,4-dichlorobenzyl)-but-2-enoic acid N-[(R)-epsilon-caprolactam-3-yl]-amide hemihydrate useful as substance P antagonists - Google Patents
Synthesis of acylaminoalkenylene amides such as (4R)-4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-4(-3,4-dichlorobenzyl)-but-2-enoic acid N-[(R)-epsilon-caprolactam-3-yl]-amide hemihydrate useful as substance P antagonistsInfo
- Publication number
- NZ571142A NZ571142A NZ571142A NZ57114207A NZ571142A NZ 571142 A NZ571142 A NZ 571142A NZ 571142 A NZ571142 A NZ 571142A NZ 57114207 A NZ57114207 A NZ 57114207A NZ 571142 A NZ571142 A NZ 571142A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- compound
- protecting group
- approx
- boc protecting
- Prior art date
Links
- CZRKBWYUKKBUMS-HNNXBMFYSA-N (4r)-4-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]-5-(3,4-dichlorophenyl)pent-2-enoic acid Chemical compound C([C@@H](N(C)C(=O)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C=CC(O)=O)C1=CC=C(Cl)C(Cl)=C1 CZRKBWYUKKBUMS-HNNXBMFYSA-N 0.000 title claims description 4
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 150000001408 amides Chemical class 0.000 title description 4
- 239000003890 substance P antagonist Substances 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- -1 CrC7-alkyl Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 13
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000012258 stirred mixture Substances 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006847 BOC protecting group Chemical group 0.000 claims 22
- WAKMMQSMEDJRRI-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC(C(Cl)=O)=CC(C(F)(F)F)=C1 WAKMMQSMEDJRRI-UHFFFAOYSA-N 0.000 claims 1
- 238000005245 sintering Methods 0.000 claims 1
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 abstract description 2
- 102100024304 Protachykinin-1 Human genes 0.000 abstract description 2
- 101800003906 Substance P Proteins 0.000 abstract description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 125000006239 protecting group Chemical group 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000002367 halogens Chemical group 0.000 description 16
- 239000000243 solution Substances 0.000 description 10
- CSARSFIKPHLXOH-GUDVDZBRSA-N tert-butyl n-[(2r,3r)-1-(3,4-dichlorophenyl)-3-hydroxy-5-oxo-5-[[(3r)-2-oxoazepan-3-yl]amino]pentan-2-yl]-n-methylcarbamate Chemical compound C([C@@H](N(C)C(=O)OC(C)(C)C)[C@H](O)CC(=O)N[C@H]1C(NCCCC1)=O)C1=CC=C(Cl)C(Cl)=C1 CSARSFIKPHLXOH-GUDVDZBRSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- DEDDLMHRYMAPEF-CQSZACIVSA-N methyl (4r)-5-(3,4-dichlorophenyl)-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-oxopentanoate Chemical compound COC(=O)CC(=O)[C@H](N(C)C(=O)OC(C)(C)C)CC1=CC=C(Cl)C(Cl)=C1 DEDDLMHRYMAPEF-CQSZACIVSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PSZOXUMUWVFQGR-ZIAGYGMSSA-N (3r,4r)-5-(3,4-dichlorophenyl)-3-hydroxy-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid Chemical compound CC(C)(C)OC(=O)N(C)[C@@H]([C@H](O)CC(O)=O)CC1=CC=C(Cl)C(Cl)=C1 PSZOXUMUWVFQGR-ZIAGYGMSSA-N 0.000 description 2
- DJSJWZIKBHZZBW-HDZMBNNRSA-N (e,4r)-5-(3,4-dichlorophenyl)-4-(methylamino)-n-[(3r)-2-oxoazepan-3-yl]pent-2-enamide Chemical compound C([C@@H](NC)\C=C\C(=O)N[C@H]1C(NCCCC1)=O)C1=CC=C(Cl)C(Cl)=C1 DJSJWZIKBHZZBW-HDZMBNNRSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- HPLJNKHMPZUEHC-HUUCEWRRSA-N methyl (3r,4r)-5-(3,4-dichlorophenyl)-3-hydroxy-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoate Chemical compound COC(=O)C[C@@H](O)[C@H](N(C)C(=O)OC(C)(C)C)CC1=CC=C(Cl)C(Cl)=C1 HPLJNKHMPZUEHC-HUUCEWRRSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012877 positron emission topography Methods 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ARMDHJYQYOUALG-GFCCVEGCSA-N (2r)-3-(3,4-dichlorophenyl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid Chemical compound CC(C)(C)OC(=O)N(C)[C@@H](C(O)=O)CC1=CC=C(Cl)C(Cl)=C1 ARMDHJYQYOUALG-GFCCVEGCSA-N 0.000 description 1
- LWXJCGXAYXXXRU-NUBCRITNSA-N (3r)-3-aminoazepan-2-one;hydrochloride Chemical compound Cl.N[C@@H]1CCCCNC1=O LWXJCGXAYXXXRU-NUBCRITNSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 125000003517 branched hexyloxy group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 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
- 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
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical group O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 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
- 150000004677 hydrates Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000004899 motility Effects 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0607532A GB0607532D0 (en) | 2006-04-13 | 2006-04-13 | Organic compounds |
| GB0610244A GB0610244D0 (en) | 2006-05-23 | 2006-05-23 | Organic compounds |
| PCT/EP2007/003213 WO2007118651A1 (en) | 2006-04-13 | 2007-04-11 | Synthesis of acylaminoalkenylene amides useful as substance p antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ571142A true NZ571142A (en) | 2011-02-25 |
Family
ID=38324102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ571142A NZ571142A (en) | 2006-04-13 | 2007-04-11 | Synthesis of acylaminoalkenylene amides such as (4R)-4-[N'-methyl-N'-(3,5-bistrifluoromethyl-benzoyl)-amino]-4(-3,4-dichlorobenzyl)-but-2-enoic acid N-[(R)-epsilon-caprolactam-3-yl]-amide hemihydrate useful as substance P antagonists |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8008479B2 (enExample) |
| EP (1) | EP2010498B1 (enExample) |
| JP (1) | JP5208917B2 (enExample) |
| KR (1) | KR20080108291A (enExample) |
| AR (1) | AR060506A1 (enExample) |
| AT (1) | ATE486853T1 (enExample) |
| AU (1) | AU2007237482B2 (enExample) |
| CA (1) | CA2645362C (enExample) |
| CL (1) | CL2007001040A1 (enExample) |
| CY (1) | CY1111294T1 (enExample) |
| DE (1) | DE602007010269D1 (enExample) |
| DK (1) | DK2010498T3 (enExample) |
| EC (1) | ECSP088820A (enExample) |
| GT (1) | GT200800209A (enExample) |
| HR (1) | HRP20110045T1 (enExample) |
| JO (1) | JO2630B1 (enExample) |
| MA (1) | MA30394B1 (enExample) |
| MX (1) | MX2008013117A (enExample) |
| MY (1) | MY145069A (enExample) |
| NO (1) | NO20084783L (enExample) |
| NZ (1) | NZ571142A (enExample) |
| PE (1) | PE20071223A1 (enExample) |
| PL (1) | PL2010498T3 (enExample) |
| PT (1) | PT2010498E (enExample) |
| RU (1) | RU2433122C2 (enExample) |
| SI (1) | SI2010498T1 (enExample) |
| TW (1) | TW200815358A (enExample) |
| WO (1) | WO2007118651A1 (enExample) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7790699B2 (en) | 2004-10-12 | 2010-09-07 | Fmc Biopolymer As | Self-gelling alginate systems and uses thereof |
| CN101273024A (zh) | 2005-07-29 | 2008-09-24 | 康瑟特制药公司 | 新颖苯并[d][1,3]-二氧杂环戊烯衍生物 |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| WO2008088727A2 (en) | 2007-01-12 | 2008-07-24 | Concert Pharmaceuticals, Inc. | Endothelin receptor antagonists |
| US8080549B2 (en) | 2007-01-12 | 2011-12-20 | Concert Pharmaceuticals, Inc. | Endothelin receptor antagonists |
| US8013007B2 (en) | 2007-02-26 | 2011-09-06 | Concert Pharmaceuticals, Inc. | Alpha 1A-adrenoceptor antagonists |
| WO2008109175A1 (en) | 2007-03-07 | 2008-09-12 | Concert Pharmaceuticals, Inc. | Deuterated piperazine derivatives as anti-anginal compounds |
| CA2681628C (en) | 2007-03-16 | 2016-10-18 | Concert Pharmaceuticals, Inc. | Inhibitors of cholesterol ester transfer protein |
| US8198305B2 (en) | 2007-04-13 | 2012-06-12 | Concert Pharmaceuticals Inc. | 1,2-benzisoxazol-3-yl compounds |
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| DK2792662T3 (da) | 2007-05-01 | 2016-07-25 | Concert Pharmaceuticals Inc | Morphinanforbindelser |
| MX370608B (es) | 2007-05-01 | 2019-12-18 | Concert Pharmaceuticals Inc | Compuestos de morfinano. |
| WO2008141021A1 (en) | 2007-05-08 | 2008-11-20 | Concert Pharmaceuticals, Inc. | Deuterated derivatives of tetrahydrotriazolopyrazine compounds and their use as dpp-iv inhibitors |
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| US7687509B2 (en) | 2007-07-09 | 2010-03-30 | Concert Pharmaceuticals Inc. | Pyrimidinecarboxamide derivatives |
| JP5389028B2 (ja) | 2007-08-14 | 2014-01-15 | コンサート ファーマシューティカルズ インコーポレイテッド | 置換オキサゾリジノン誘導体 |
| JP2010537717A (ja) | 2007-08-28 | 2010-12-09 | エフ エム シー コーポレーション | 遅効性自己ゲル化アルギネートシステムおよびその用途 |
| MX2010002679A (es) | 2007-09-12 | 2010-03-29 | Concert Pharmaceuticals Inc | Derivados de 4-oxoquinolina deuterados para el tratamiento de la infeccion por el virus de inmunodeficiencia humana. |
| JP5647519B2 (ja) | 2007-09-13 | 2014-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | 重水素化カテコールおよびベンゾ［ｄ］［１，３］ジオキソールおよびその誘導体の合成 |
| EP2212298B1 (en) | 2007-10-18 | 2013-03-27 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| US8592487B2 (en) | 2007-10-26 | 2013-11-26 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| US8084464B2 (en) | 2007-12-18 | 2011-12-27 | Concert Pharmaceuticals, Inc. | Tetrahydroisoquinoline derivatives |
| US8609673B2 (en) | 2008-01-22 | 2013-12-17 | Concert Pharmaceuticals, Inc. | Vandetanib derivatives |
| US7855204B2 (en) | 2008-01-22 | 2010-12-21 | Concert Pharmaceuticals Inc. | Derivatives of gefitinib |
| KR20100121527A (ko) | 2008-02-29 | 2010-11-17 | 콘서트 파마슈티컬즈, 인크. | 치환된 잔틴 유도체 |
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| EP2334621A1 (en) | 2008-09-16 | 2011-06-22 | Concert Pharmaceuticals, Inc. | Deuterated 2-amino-3-hydroxypropanoic acid derivatives |
| JP5730769B2 (ja) | 2008-09-19 | 2015-06-10 | コンサート ファーマシューティカルズ インコーポレイテッド | モルヒナン化合物 |
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| HUE047354T2 (hu) | 2011-05-18 | 2020-04-28 | Vertex Pharmaceuticals Europe Ltd | Ivacaftor deuterizált származékai |
| CN104364255A (zh) | 2012-04-13 | 2015-02-18 | 康塞特医药品有限公司 | 取代的黄嘌呤衍生物 |
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| WO2015120393A1 (en) | 2014-02-10 | 2015-08-13 | Concert Pharmaceuticals, Inc. | Substituted triazolobenzodiazepines |
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| US10196384B2 (en) | 2015-03-31 | 2019-02-05 | Vertex Pharmaceuticals (Europe) Limited | Deuterated CFTR modulators |
| WO2016176335A1 (en) | 2015-04-27 | 2016-11-03 | Concert Pharmaceuticals, Inc. | Deuterated otx-015 |
| HK1258473A1 (zh) | 2015-09-25 | 2019-11-15 | Vertex Pharmaceuticals (Europe) Limited | 氘代cftr增效剂 |
| EP3377179B1 (en) | 2015-11-19 | 2021-04-07 | Concert Pharmaceuticals Inc. | Deuterated epi-743 |
| US10442761B2 (en) | 2016-02-16 | 2019-10-15 | Concert Pharmaceuticals, Inc. | Deuterated GFT-505 |
| CA3082834A1 (en) | 2017-11-22 | 2019-05-31 | Concert Pharmaceuticals, Inc. | Deuterated analogs of d-serine and uses thereof |
| WO2019109021A1 (en) | 2017-12-01 | 2019-06-06 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| WO2020206367A1 (en) | 2019-04-03 | 2020-10-08 | Concert Pharmaceuticals, Inc. | Processes for the preparation of deuterated d-serine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69602087T2 (de) | 1995-02-22 | 1999-09-09 | Novartis Ag | 1-aryl-2-acylamino-ethan-verbindungen und ihre verwendung als neurokinin- insbesondere als neurokinin-1-antagonisten |
| MY132550A (en) * | 1996-08-22 | 2007-10-31 | Novartis Ag | Acylaminoalkenylene-amide derivatives as nk1 and nk2 antogonists |
| GB0010958D0 (en) * | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
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2007
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- 2007-04-11 AU AU2007237482A patent/AU2007237482B2/en not_active Ceased
- 2007-04-11 PT PT07724154T patent/PT2010498E/pt unknown
- 2007-04-11 EP EP07724154A patent/EP2010498B1/en not_active Not-in-force
- 2007-04-11 RU RU2008145102/04A patent/RU2433122C2/ru not_active IP Right Cessation
- 2007-04-11 PE PE2007000444A patent/PE20071223A1/es not_active Application Discontinuation
- 2007-04-11 KR KR1020087024839A patent/KR20080108291A/ko not_active Ceased
- 2007-04-11 JP JP2009504637A patent/JP5208917B2/ja not_active Expired - Fee Related
- 2007-04-11 HR HR20110045T patent/HRP20110045T1/hr unknown
- 2007-04-11 AT AT07724154T patent/ATE486853T1/de active
- 2007-04-11 SI SI200730483T patent/SI2010498T1/sl unknown
- 2007-04-11 US US12/296,969 patent/US8008479B2/en not_active Expired - Fee Related
- 2007-04-11 AR ARP070101533A patent/AR060506A1/es not_active Application Discontinuation
- 2007-04-11 DK DK07724154.5T patent/DK2010498T3/da active
- 2007-04-11 CA CA2645362A patent/CA2645362C/en not_active Expired - Fee Related
- 2007-04-11 DE DE602007010269T patent/DE602007010269D1/de active Active
- 2007-04-11 WO PCT/EP2007/003213 patent/WO2007118651A1/en not_active Ceased
- 2007-04-11 PL PL07724154T patent/PL2010498T3/pl unknown
- 2007-04-11 MX MX2008013117A patent/MX2008013117A/es active IP Right Grant
- 2007-04-11 NZ NZ571142A patent/NZ571142A/en not_active IP Right Cessation
- 2007-04-12 TW TW096112886A patent/TW200815358A/zh unknown
- 2007-04-12 CL CL200701040A patent/CL2007001040A1/es unknown
-
2008
- 2008-10-08 MY MYPI20083997A patent/MY145069A/en unknown
- 2008-10-10 GT GT200800209A patent/GT200800209A/es unknown
- 2008-10-13 EC EC2008008820A patent/ECSP088820A/es unknown
- 2008-11-03 MA MA31347A patent/MA30394B1/fr unknown
- 2008-11-12 NO NO20084783A patent/NO20084783L/no not_active Application Discontinuation
-
2011
- 2011-01-26 CY CY20111100082T patent/CY1111294T1/el unknown
- 2011-07-22 US US13/188,795 patent/US20110282053A1/en not_active Abandoned
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