UA62993C2 - CHROMAN DERIVATIVES SUBSTITUTED ON CARBOXYLIC GROUP USED AS AGONISTS OF b-3-ADRENORECEPTOR - Google Patents

CHROMAN DERIVATIVES SUBSTITUTED ON CARBOXYLIC GROUP USED AS AGONISTS OF b-3-ADRENORECEPTOR Download PDF

Info

Publication number: UA62993C2
Authority: UA; Ukraine
Prior art keywords: carbon atoms; group; compound; alkyl; mixture
Prior art date: 1997-12-19

Application number

UA2000074336A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-12-19

Filing date

1998-12-16

Publication date

2004-01-15

1998-12-16 Application filed by Bayer Ag filed Critical Bayer Ag

2004-01-15 Publication of UA62993C2 publication Critical patent/UA62993C2/uk

Links

VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical group C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract description 11
239000000556 agonist Substances 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 104
239000000203 mixture Substances 0.000 claims description 72
238000000034 method Methods 0.000 claims description 44
-1 oxo- Chemical class 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 30
150000002148 esters Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 11
150000004820 halides Chemical class 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 9
239000012634 fragment Substances 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
208000008589 Obesity Diseases 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
235000020824 obesity Nutrition 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000004001 thioalkyl group Chemical group 0.000 claims description 4
KJNLSEOJEFDELT-JJNLEZRASA-N [2-[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-2-oxoethyl]phosphonic acid Chemical group C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COC(=O)CP(O)(O)=O)[C@@H](O)[C@H]1O KJNLSEOJEFDELT-JJNLEZRASA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
230000001270 agonistic effect Effects 0.000 claims 1
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 1
102000005962 receptors Human genes 0.000 abstract description 11
230000001404 mediated effect Effects 0.000 abstract description 10
108020003175 receptors Proteins 0.000 abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 38
239000007787 solid Substances 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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235000019441 ethanol Nutrition 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
229960000583 acetic acid Drugs 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 13
235000014113 dietary fatty acids Nutrition 0.000 description 13
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229920006395 saturated elastomer Polymers 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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239000003921 oil Substances 0.000 description 12
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150000004665 fatty acids Chemical class 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
150000002924 oxiranes Chemical class 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
229940079593 drug Drugs 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000002798 polar solvent Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 8
102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
230000001575 pathological effect Effects 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000003599 detergent Substances 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical class C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 5
108060003345 Adrenergic Receptor Proteins 0.000 description 5
102000017910 Adrenergic receptor Human genes 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
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229910052740 iodine Inorganic materials 0.000 description 5
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230000000638 stimulation Effects 0.000 description 5
239000000375 suspending agent Substances 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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229920001206 natural gum Polymers 0.000 description 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
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LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
239000001814 pectin Substances 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960003418 phenoxybenzamine Drugs 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000006187 pill Substances 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
208000017497 prostate disease Diseases 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229960002385 streptomycin sulfate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
229940125670 thienopyridine Drugs 0.000 description 1
239000002175 thienopyridine Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
238000013271 transdermal drug delivery Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
208000014001 urinary system disease Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000000636 white adipocyte Anatomy 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Obesity (AREA)
Hematology (AREA)
Biomedical Technology (AREA)
Child & Adolescent Psychology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Detergent Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Pyrrole Compounds (AREA)

UA2000074336A 1997-12-19 1998-12-16 CHROMAN DERIVATIVES SUBSTITUTED ON CARBOXYLIC GROUP USED AS AGONISTS OF b-3-ADRENORECEPTOR UA62993C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US99462097A	1997-12-19	1997-12-19
PCT/US1998/026735 WO1999032476A1 (en)	1997-12-19	1998-12-16	Carboxyl substituted chroman derivatives useful as beta 3 adrenoreceptor agonists

Publications (1)

Publication Number	Publication Date
UA62993C2 true UA62993C2 (en)	2004-01-15

Family

ID=25540853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2000074336A UA62993C2 (en)	1997-12-19	1998-12-16	CHROMAN DERIVATIVES SUBSTITUTED ON CARBOXYLIC GROUP USED AS AGONISTS OF b-3-ADRENORECEPTOR

Country Status (24)

Country	Link
EP (1)	EP1040106B1 (id)
JP (1)	JP2001526282A (id)
KR (1)	KR20010033188A (id)
CN (1)	CN1284952A (id)
AT (1)	ATE222901T1 (id)
AU (1)	AU749097B2 (id)
BG (1)	BG104593A (id)
BR (1)	BR9814302A (id)
CA (1)	CA2316971A1 (id)
DE (1)	DE69807523T2 (id)
DK (1)	DK1040106T3 (id)
ES (1)	ES2183434T3 (id)
HU (1)	HUP0004565A3 (id)
ID (1)	ID26524A (id)
IL (1)	IL136689A0 (id)
NO (1)	NO20003083L (id)
NZ (1)	NZ505200A (id)
PL (1)	PL341229A1 (id)
PT (1)	PT1040106E (id)
RU (1)	RU2223269C2 (id)
SK (1)	SK9362000A3 (id)
TR (1)	TR200001927T2 (id)
UA (1)	UA62993C2 (id)
WO (1)	WO1999032476A1 (id)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR035605A1 (es)	2000-12-11	2004-06-16	Bayer Corp	Derivados de aminometil cromano di-sustituidos, un metodo para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la manufactura de medicamentos utiles como agonistas beta-3-adreno-receptores
AR035858A1 (es) *	2001-04-23	2004-07-21	Bayer Corp	Derivados de cromano 2,6-sustituidos,composiciones farmaceuticas,uso de dichos derivados para la manufactura de medicamentos utiles como agonistas adrenorreceptores beta-3
US20040265991A1 (en) *	2001-10-17	2004-12-30	Naoaki Taoka	Process for preparation of (s)-alpha-halomethylpyridine-methanol derivatives
MY147767A (en) *	2004-06-16	2013-01-31	Janssen Pharmaceutica Nv	Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders
JP2008530229A (ja)	2005-02-17	2008-08-07	ワイス	シクロアルキル縮合インドール、ベンゾチオフェン、ベンゾフランおよびインデン誘導体
EP1803716B1 (en) *	2005-12-28	2012-07-25	Acino Pharma AG	A process for preparation of racemic nebivolol
RU2392277C2 (ru) *	2005-12-28	2010-06-20	Асино Фарма Аг	Способ получения рацемического небиволола
US7560575B2 (en)	2005-12-28	2009-07-14	Acino Pharma Ag	Process for preparation of racemic Nebivolol
ES2534336B1 (es) *	2013-10-18	2016-01-28	Artax Biopharma Inc.	Derivados de cromeno como inhibidores de la interacción TCR-Nck
ES2534318B1 (es) *	2013-10-18	2016-01-28	Artax Biopharma Inc.	Derivados de cromeno sustituidos por alcóxido como inhibidores de la interacción TCR-Nck

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1337429C (en) *	1983-12-05	1995-10-24	Guy Rosalia Eugene Van Lommen	Derivatives of 2,2'-iminobisethanol
GB8801306D0 (en) *	1988-01-21	1988-02-17	Ici Plc	Chemical compounds
UA35545C2 (uk) *	1991-04-08	2001-04-16	Джон Вайс Енд Бразер Лімітед	Спосіб одержання похідних 4-оксохіноліну або хромону
US5451677A (en) *	1993-02-09	1995-09-19	Merck & Co., Inc.	Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity
ATE154935T1 (de) *	1993-06-14	1997-07-15	Pfizer	Zweite amine als antidiabetische mittel und für die behandlung von fettleibigkeit
GB9405019D0 (en) *	1994-03-15	1994-04-27	Smithkline Beecham Plc	Novel compounds
US5561142A (en) *	1994-04-26	1996-10-01	Merck & Co., Inc.	Substituted sulfonamides as selective β3 agonists for the treatment of diabetes and obesity
EP0801060A1 (en) *	1996-04-09	1997-10-15	Pfizer Inc.	Heterocyclic Beta-3 Adrenergenic Agonists

1998
- 1998-12-16 DK DK98963240T patent/DK1040106T3/da active
- 1998-12-16 RU RU2000119110/04A patent/RU2223269C2/ru not_active IP Right Cessation
- 1998-12-16 ES ES98963240T patent/ES2183434T3/es not_active Expired - Lifetime
- 1998-12-16 NZ NZ505200A patent/NZ505200A/xx unknown
- 1998-12-16 CA CA002316971A patent/CA2316971A1/en not_active Abandoned
- 1998-12-16 WO PCT/US1998/026735 patent/WO1999032476A1/en not_active Ceased
- 1998-12-16 DE DE69807523T patent/DE69807523T2/de not_active Expired - Fee Related
- 1998-12-16 UA UA2000074336A patent/UA62993C2/uk unknown
- 1998-12-16 PT PT98963240T patent/PT1040106E/pt unknown
- 1998-12-16 CN CN98813619A patent/CN1284952A/zh active Pending
- 1998-12-16 PL PL98341229A patent/PL341229A1/xx not_active Application Discontinuation
- 1998-12-16 EP EP98963240A patent/EP1040106B1/en not_active Expired - Lifetime
- 1998-12-16 AU AU18300/99A patent/AU749097B2/en not_active Ceased
- 1998-12-16 TR TR2000/01927T patent/TR200001927T2/xx unknown
- 1998-12-16 BR BR9814302-6A patent/BR9814302A/pt not_active IP Right Cessation
- 1998-12-16 AT AT98963240T patent/ATE222901T1/de not_active IP Right Cessation
- 1998-12-16 JP JP2000525413A patent/JP2001526282A/ja not_active Withdrawn
- 1998-12-16 ID IDW20001393A patent/ID26524A/id unknown
- 1998-12-16 HU HU0004565A patent/HUP0004565A3/hu unknown
- 1998-12-16 KR KR1020007006572A patent/KR20010033188A/ko not_active Ceased
- 1998-12-16 IL IL13668998A patent/IL136689A0/xx unknown
- 1998-12-16 SK SK936-2000A patent/SK9362000A3/sk unknown
2000
- 2000-06-15 NO NO20003083A patent/NO20003083L/no not_active Application Discontinuation
- 2000-07-11 BG BG104593A patent/BG104593A/xx unknown

Also Published As

Publication number	Publication date
AU749097B2 (en)	2002-06-20
RU2223269C2 (ru)	2004-02-10
WO1999032476A1 (en)	1999-07-01
ID26524A (id)	2001-01-11
ES2183434T3 (es)	2003-03-16
PT1040106E (pt)	2002-11-29
ATE222901T1 (de)	2002-09-15
NO20003083L (no)	2000-08-15
KR20010033188A (ko)	2001-04-25
EP1040106A1 (en)	2000-10-04
HUP0004565A2 (hu)	2001-08-28
JP2001526282A (ja)	2001-12-18
AU1830099A (en)	1999-07-12
BR9814302A (pt)	2000-10-10
EP1040106B1 (en)	2002-08-28
SK9362000A3 (en)	2001-09-11
TR200001927T2 (tr)	2001-06-21
DE69807523D1 (de)	2002-10-02
CA2316971A1 (en)	1999-07-01
DE69807523T2 (de)	2003-01-09
IL136689A0 (en)	2001-06-14
DK1040106T3 (da)	2002-12-02
PL341229A1 (en)	2001-03-26
CN1284952A (zh)	2001-02-21
HUP0004565A3 (en)	2002-12-28
BG104593A (en)	2001-09-28
NZ505200A (en)	2002-09-27
NO20003083D0 (no)	2000-06-15

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