NO970372L - Aroyloksy- og aroyltiopropanolamin-derivater anvendelige som <beta>-3-adrenoreseptor-agonister og antagonister for <beta>-1-og-<beta>-2-adrenoreseptorer og farmasöytiske blandinger derav - Google Patents
Aroyloksy- og aroyltiopropanolamin-derivater anvendelige som <beta>-3-adrenoreseptor-agonister og antagonister for <beta>-1-og-<beta>-2-adrenoreseptorer og farmasöytiske blandinger deravInfo
- Publication number
- NO970372L NO970372L NO970372A NO970372A NO970372L NO 970372 L NO970372 L NO 970372L NO 970372 A NO970372 A NO 970372A NO 970372 A NO970372 A NO 970372A NO 970372 L NO970372 L NO 970372L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid
- compound
- group
- ester
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 59
- 239000000556 agonist Substances 0.000 title description 7
- 239000005557 antagonist Substances 0.000 title description 5
- 125000005333 aroyloxy group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 481
- 238000000034 method Methods 0.000 claims description 431
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 113
- -1 hydroxy, hydroxymethyl Chemical group 0.000 claims description 99
- 150000002148 esters Chemical class 0.000 claims description 94
- 239000002253 acid Substances 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000012453 solvate Substances 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 32
- 150000001408 amides Chemical class 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 241000282412 Homo Species 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 7
- 230000003000 nontoxic effect Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
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- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 208000028774 intestinal disease Diseases 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- GNOKWJFBPJGLEE-UHFFFAOYSA-N 2-[4-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]propyl]phenoxy]acetic acid Chemical compound C=1C=C(O)C=CC=1OCC(O)CNC(C)CC1=CC=C(OCC(O)=O)C=C1 GNOKWJFBPJGLEE-UHFFFAOYSA-N 0.000 claims description 4
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 claims description 2
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 230000035879 hyperinsulinaemia Effects 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 238000005728 strengthening Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 267
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 213
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 67
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- 239000002904 solvent Substances 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- 239000012043 crude product Substances 0.000 description 59
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 57
- 238000000746 purification Methods 0.000 description 55
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 45
- 239000003921 oil Substances 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 238000004587 chromatography analysis Methods 0.000 description 41
- 125000004494 ethyl ester group Chemical group 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 239000000741 silica gel Substances 0.000 description 38
- 229910002027 silica gel Inorganic materials 0.000 description 38
- 239000007787 solid Substances 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 229910052786 argon Inorganic materials 0.000 description 29
- 238000010828 elution Methods 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 229910003002 lithium salt Inorganic materials 0.000 description 19
- 159000000002 lithium salts Chemical class 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 16
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- 238000004108 freeze drying Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
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- 239000000284 extract Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical class P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 11
- 125000006308 propyl amino group Chemical group 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
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- 229930040373 Paraformaldehyde Natural products 0.000 description 10
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- 229920002866 paraformaldehyde Polymers 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 8
- 102000015779 HDL Lipoproteins Human genes 0.000 description 8
- 108010010234 HDL Lipoproteins Proteins 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- AFLQPBANDWKDPM-SSDOTTSWSA-N [(2r)-1-(4-hydroxyphenyl)propan-2-yl]carbamic acid Chemical compound OC(=O)N[C@H](C)CC1=CC=C(O)C=C1 AFLQPBANDWKDPM-SSDOTTSWSA-N 0.000 description 8
- AIHIHVZYAAMDPM-QMMMGPOBSA-N [(2s)-oxiran-2-yl]methyl 3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)OC[C@H]2OC2)=C1 AIHIHVZYAAMDPM-QMMMGPOBSA-N 0.000 description 8
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 8
- GTTBQSNGUYHPNK-UHFFFAOYSA-N hydroxymethylphosphonic acid Chemical compound OCP(O)(O)=O GTTBQSNGUYHPNK-UHFFFAOYSA-N 0.000 description 8
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- OTNZYOGAUQIRQU-UHFFFAOYSA-N (4-chlorophenyl)sulfonyloxymethylphosphonic acid Chemical compound OP(O)(=O)COS(=O)(=O)C1=CC=C(Cl)C=C1 OTNZYOGAUQIRQU-UHFFFAOYSA-N 0.000 description 7
- PMOQQERBOQJYOE-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethylcarbamic acid Chemical compound OC(=O)NCCC1=CC=C(O)C=C1 PMOQQERBOQJYOE-UHFFFAOYSA-N 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
- GPQVWOYODKOIAS-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-[4-hydroxy-3-(hydroxymethyl)phenoxy]propyl]amino]propyl]phenoxy]methylphosphonic acid Chemical compound C=1C=C(O)C(CO)=CC=1OCC(O)CNC(C)CC1=CC=C(OCP(O)(O)=O)C=C1 GPQVWOYODKOIAS-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
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- BYDXZYUGDXYSJY-MRXNPFEDSA-N (2s)-2-[(4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C([C@H]1OC1)OC(C=C1)=CC=C1OCC1=CC=CC=C1 BYDXZYUGDXYSJY-MRXNPFEDSA-N 0.000 description 6
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- KMFBZISDQJVZMF-MRVPVSSYSA-N [4-[(2r)-2-aminopropyl]phenoxy]methylphosphonic acid Chemical compound C[C@@H](N)CC1=CC=C(OCP(O)(O)=O)C=C1 KMFBZISDQJVZMF-MRVPVSSYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
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- 238000009835 boiling Methods 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- KIUBHBBIKJOLIK-INIZCTEOSA-N [4-[2-[[(2s)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenoxy]methylphosphonic acid Chemical compound C([C@H](O)COC=1C=CC(O)=CC=1)NCCC1=CC=C(OCP(O)(O)=O)C=C1 KIUBHBBIKJOLIK-INIZCTEOSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 5
- 238000011321 prophylaxis Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
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- 125000005907 alkyl ester group Chemical group 0.000 description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- SHNUAJCQFNVFIE-UHFFFAOYSA-O hexyl-hydroxy-oxophosphanium Chemical compound CCCCCC[P+](O)=O SHNUAJCQFNVFIE-UHFFFAOYSA-O 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 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 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000003512 tremorgenic effect Effects 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/303—Cycloaliphatic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3223—Esters of cycloaliphatic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9415304A GB9415304D0 (en) | 1994-07-29 | 1994-07-29 | Novel compounds |
GB9423179A GB9423179D0 (en) | 1994-11-17 | 1994-11-17 | Novel compounds |
GBGB9510485.7A GB9510485D0 (en) | 1995-05-24 | 1995-05-24 | Novel compounds |
PCT/EP1995/003037 WO1996004233A1 (en) | 1994-07-29 | 1995-07-27 | Aryloxy and arylthiopropanolamine derivatives useful as beta 3-adrenoreceptor agonists and antagonists of the beta 1 and beta 2-adrenoreceptors and pharmaceutical composition thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
NO970372D0 NO970372D0 (no) | 1997-01-28 |
NO970372L true NO970372L (no) | 1997-03-18 |
Family
ID=27267307
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO970372A NO970372L (no) | 1994-07-29 | 1997-01-28 | Aroyloksy- og aroyltiopropanolamin-derivater anvendelige som <beta>-3-adrenoreseptor-agonister og antagonister for <beta>-1-og-<beta>-2-adrenoreseptorer og farmasöytiske blandinger derav |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0772585A1 (cs) |
JP (1) | JPH10503507A (cs) |
CN (1) | CN1159797A (cs) |
AU (1) | AU3254695A (cs) |
BR (1) | BR9508991A (cs) |
CA (1) | CA2196193A1 (cs) |
CZ (1) | CZ25597A3 (cs) |
HU (1) | HUT76800A (cs) |
MX (1) | MX9700765A (cs) |
NO (1) | NO970372L (cs) |
PL (1) | PL318381A1 (cs) |
WO (1) | WO1996004233A1 (cs) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9605495D0 (en) * | 1996-03-15 | 1996-05-15 | Smithkline Beecham Plc | Novel compounds |
US5914339A (en) * | 1996-05-14 | 1999-06-22 | American Home Products Corporation | Substituted 1,3-benzodioxoles |
EP0827746B1 (en) | 1996-09-05 | 2002-04-03 | Eli Lilly And Company | Carbazole analogues as selective beta3 adrenergic agonists |
WO1998022480A1 (en) * | 1996-11-18 | 1998-05-28 | Smithkline Beecham Plc | Phosphorus containing aryloxy or arylthio propanolamine derivatives |
GB9703492D0 (en) * | 1997-02-20 | 1997-04-09 | Smithkline Beecham Plc | Novel compounds |
CO5011072A1 (es) * | 1997-12-05 | 2001-02-28 | Lilly Co Eli | Etanolaminas pirazinil substituidas como agfonistas de los receptores |
CA2285213C (en) * | 1998-01-30 | 2013-07-30 | Boulder Scientific Company | Silylated and n-silylated compound synthesis |
ATE423555T1 (de) * | 1998-04-06 | 2009-03-15 | Astellas Pharma Inc | Verwendung von beta-3-adrenergen-rezeptoren agonisten in der behandlung von dysurie |
AUPP549998A0 (en) * | 1998-08-26 | 1998-09-17 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
US7098248B2 (en) | 2001-07-09 | 2006-08-29 | Research Development Foundation | Beta-adrenergic blockade reversal of catabolism after severe burn |
DE102008064003A1 (de) * | 2008-12-19 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von mono-funktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
CN107266341B (zh) * | 2017-06-23 | 2020-01-07 | 华东师范大学 | 芳氧基取代丙-2-醇胺的衍生物作为β3肾上腺素能受体拮抗剂、制备方法和用途 |
CN112442167A (zh) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | 一种反应型阻燃剂及其制备方法和应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1262729A (en) * | 1983-10-19 | 1989-11-07 | Leo Alig | Phenoxypropanolamines |
EP0300290B1 (de) * | 1987-07-21 | 1991-12-18 | F. Hoffmann-La Roche Ag | Phenoxypropanolamine |
GB8801306D0 (en) * | 1988-01-21 | 1988-02-17 | Ici Plc | Chemical compounds |
GB9215844D0 (en) * | 1992-07-25 | 1992-09-09 | Smithkline Beecham Plc | Novel compounds |
-
1995
- 1995-07-27 HU HU9700262A patent/HUT76800A/hu unknown
- 1995-07-27 AU AU32546/95A patent/AU3254695A/en not_active Abandoned
- 1995-07-27 PL PL95318381A patent/PL318381A1/xx unknown
- 1995-07-27 BR BR9508991A patent/BR9508991A/pt not_active Application Discontinuation
- 1995-07-27 WO PCT/EP1995/003037 patent/WO1996004233A1/en not_active Application Discontinuation
- 1995-07-27 EP EP95929029A patent/EP0772585A1/en not_active Withdrawn
- 1995-07-27 JP JP8506193A patent/JPH10503507A/ja active Pending
- 1995-07-27 CZ CZ97255A patent/CZ25597A3/cs unknown
- 1995-07-27 CA CA002196193A patent/CA2196193A1/en not_active Abandoned
- 1995-07-27 MX MX9700765A patent/MX9700765A/es unknown
- 1995-07-27 CN CN95195371A patent/CN1159797A/zh active Pending
-
1997
- 1997-01-28 NO NO970372A patent/NO970372L/no unknown
Also Published As
Publication number | Publication date |
---|---|
JPH10503507A (ja) | 1998-03-31 |
MX9700765A (es) | 1997-05-31 |
HUT76800A (en) | 1997-11-28 |
WO1996004233A1 (en) | 1996-02-15 |
CZ25597A3 (cs) | 1998-02-18 |
NO970372D0 (no) | 1997-01-28 |
AU3254695A (en) | 1996-03-04 |
BR9508991A (pt) | 1997-10-21 |
EP0772585A1 (en) | 1997-05-14 |
CN1159797A (zh) | 1997-09-17 |
PL318381A1 (en) | 1997-06-09 |
CA2196193A1 (en) | 1996-02-15 |
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