NO872094L - Fremgangsmaate for fremstilling av dbh-inhiberende forbindelser. - Google Patents

Fremgangsmaate for fremstilling av dbh-inhiberende forbindelser.

Info

Publication number: NO872094L
Authority: NO; Norway
Prior art keywords: triazole; compounds; formula; thiol; dbh
Prior art date: 1986-05-23

Application number

NO872094A

Other languages

English (en)

Norwegian (no)

Other versions

NO872094D0 (no

Inventor

Joseph Alan Finkelstein

Lawrence Ivan Kruse

Original Assignee

Smithkline Beckman Corp

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.)

1986-05-23

Filing date

1987-05-19

Publication date

1987-11-24

1987-05-19 Application filed by Smithkline Beckman Corp filed Critical Smithkline Beckman Corp

1987-05-19 Publication of NO872094D0 publication Critical patent/NO872094D0/no

1987-11-24 Publication of NO872094L publication Critical patent/NO872094L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 48
238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
CNCIIDBWAGTBLU-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-1h-1,2,4-triazole-3-thione Chemical compound FC1=CC=CC(CN2C(=NC=N2)S)=C1 CNCIIDBWAGTBLU-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
CSENNVXEEZFGAX-UHFFFAOYSA-N 2-[(3,5-difluorophenyl)methyl]-1h-1,2,4-triazole-3-thione Chemical compound FC1=CC(F)=CC(CN2C(=NC=N2)S)=C1 CSENNVXEEZFGAX-UHFFFAOYSA-N 0.000 claims description 5
WZTKDLGTNHUCMI-UHFFFAOYSA-N 2-benzyl-1h-1,2,4-triazole-3-thione Chemical compound SC1=NC=NN1CC1=CC=CC=C1 WZTKDLGTNHUCMI-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
FQLJXDMZMYWLJW-UHFFFAOYSA-N tert-butyl n-[(3-fluorophenyl)methylamino]carbamate Chemical compound CC(C)(C)OC(=O)NNCC1=CC=CC(F)=C1 FQLJXDMZMYWLJW-UHFFFAOYSA-N 0.000 claims description 5
ZFWFRTVIIMTOLY-UHFFFAOYSA-N 2-isothiocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=S ZFWFRTVIIMTOLY-UHFFFAOYSA-N 0.000 claims description 4
229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000565 sulfonamide group Chemical group 0.000 claims description 4
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
IFKBCOUZOBUWGF-UHFFFAOYSA-N tert-butyl n-[tert-butylcarbamothioyl-[(3-fluorophenyl)methyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NN(C(=S)NC(C)(C)C)CC1=CC=CC(F)=C1 IFKBCOUZOBUWGF-UHFFFAOYSA-N 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
NXGRHCFNYDZNRF-UHFFFAOYSA-N tert-butyl n-[(3,5-difluorophenyl)methylamino]carbamate Chemical compound CC(C)(C)OC(=O)NNCC1=CC(F)=CC(F)=C1 NXGRHCFNYDZNRF-UHFFFAOYSA-N 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
OPVJBJKJBHTNCE-UHFFFAOYSA-N tert-butyl n-(benzylamino)carbamate Chemical compound CC(C)(C)OC(=O)NNCC1=CC=CC=C1 OPVJBJKJBHTNCE-UHFFFAOYSA-N 0.000 claims 1
UPLCFDFFTSGQLL-UHFFFAOYSA-N tert-butyl n-[benzyl(tert-butylcarbamothioyl)amino]carbamate Chemical compound CC(C)(C)OC(=O)NN(C(=S)NC(C)(C)C)CC1=CC=CC=C1 UPLCFDFFTSGQLL-UHFFFAOYSA-N 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003112 inhibitor Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
-1 2-substituted-1-t-butoxycarbonyl-4-t-butylthiosemicarbazides Chemical class 0.000 description 10
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical class CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000000203 mixture Substances 0.000 description 6
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 5
230000036772 blood pressure Effects 0.000 description 5
150000003943 catecholamines Chemical class 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
229960002748 norepinephrine Drugs 0.000 description 5
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000003935 benzaldehydes Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 3
238000012360 testing method Methods 0.000 description 3
230000000304 vasodilatating effect Effects 0.000 description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
QHGUCRYDKWKLMG-QMMMGPOBSA-N (R)-octopamine Chemical compound NC[C@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-QMMMGPOBSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
RYEMLDJRAYNPOF-UHFFFAOYSA-N 2-(3-nitrophenyl)-1h-1,2,4-triazole-3-thione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N=CN2)=S)=C1 RYEMLDJRAYNPOF-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
ASOFZHSTJHGQDT-UHFFFAOYSA-N 3,5-difluorobenzaldehyde Chemical compound FC1=CC(F)=CC(C=O)=C1 ASOFZHSTJHGQDT-UHFFFAOYSA-N 0.000 description 2
PMXUQLPINCSZPA-UHFFFAOYSA-N 3-[(3-sulfanylidene-1h-1,2,4-triazol-2-yl)methyl]benzonitrile Chemical compound S=C1N=CNN1CC1=CC=CC(C#N)=C1 PMXUQLPINCSZPA-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
241000282412 Homo Species 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
QHGUCRYDKWKLMG-MRVPVSSYSA-N Octopamine Natural products NC[C@@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-MRVPVSSYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
229940127088 antihypertensive drug Drugs 0.000 description 2
230000008901 benefit Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
239000011575 calcium Substances 0.000 description 2
PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 2
230000003177 cardiotonic effect Effects 0.000 description 2
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229910052801 chlorine Inorganic materials 0.000 description 2
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WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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239000003937 drug carrier Substances 0.000 description 2
YKNHZLAHZQSMFK-UHFFFAOYSA-N ethyl 4-[(3-sulfanylidene-1h-1,2,4-triazol-2-yl)methyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1CN1C(=S)N=CN1 YKNHZLAHZQSMFK-UHFFFAOYSA-N 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
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235000011852 gelatine desserts Nutrition 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
230000001452 natriuretic effect Effects 0.000 description 2
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150000007524 organic acids Chemical class 0.000 description 2
150000004031 phenylhydrazines Chemical class 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
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238000010992 reflux Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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VCIYYGKFOLVOEN-UHFFFAOYSA-N tert-butyl n-[tert-butylcarbamothioyl-[(3,5-difluorophenyl)methyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NN(C(=S)NC(C)(C)C)CC1=CC(F)=CC(F)=C1 VCIYYGKFOLVOEN-UHFFFAOYSA-N 0.000 description 2
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RQPKNXVVIBYOBX-KDBLBPRBSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid;(2s)-2-(dihydroxyamino)-3-phenylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1.ON(O)[C@H](C(O)=O)CC1=CC=CC=C1 RQPKNXVVIBYOBX-KDBLBPRBSA-N 0.000 description 1
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WDJARUKOMOGTHA-UHFFFAOYSA-N 5-aminopyridine-2-carboxylic acid Chemical compound NC1=CC=C(C(O)=O)N=C1 WDJARUKOMOGTHA-UHFFFAOYSA-N 0.000 description 1
NGLVRRCCMNBLFN-UHFFFAOYSA-N 5-butanoylpyridine-2-carboxylic acid Chemical compound CCCC(=O)C1=CC=C(C(O)=O)N=C1 NGLVRRCCMNBLFN-UHFFFAOYSA-N 0.000 description 1
PWPODTNJDOITDE-UHFFFAOYSA-N 5-hydrazinylpyridine-2-carboxylic acid Chemical compound NNC1=CC=C(C(O)=O)N=C1 PWPODTNJDOITDE-UHFFFAOYSA-N 0.000 description 1
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239000008187 granular material Substances 0.000 description 1
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230000003082 hepatotoxic effect Effects 0.000 description 1
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239000002035 hexane extract Substances 0.000 description 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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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 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
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DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO872094A 1986-05-23 1987-05-19 Fremgangsmaate for fremstilling av dbh-inhiberende forbindelser. NO872094L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US86643786A	1986-05-23	1986-05-23

Publications (2)

Publication Number	Publication Date
NO872094D0 NO872094D0 (no)	1987-05-19
NO872094L true NO872094L (no)	1987-11-24

Family

ID=25347617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO872094A NO872094L (no)	1986-05-23	1987-05-19	Fremgangsmaate for fremstilling av dbh-inhiberende forbindelser.

Country Status (15)

Country	Link
EP (1)	EP0246888A3 (de)
JP (1)	JPS62283967A (de)
KR (1)	KR870011109A (de)
CN (1)	CN87103808A (de)
AU (1)	AU7334487A (de)
DK (1)	DK251087A (de)
FI (1)	FI872249L (de)
HU (1)	HU201530B (de)
IL (1)	IL82542A0 (de)
NO (1)	NO872094L (de)
NZ (1)	NZ220347A (de)
PH (1)	PH23506A (de)
PT (1)	PT84904B (de)
ZA (1)	ZA873653B (de)
ZW (1)	ZW9087A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4628059A (en) *	1985-10-31	1986-12-09	Smithklein Beckman Corporation	Dopamine-β-hydroxylase inhibitors
DE4230466A1 (de) *	1992-09-11	1994-03-17	Basf Ag	Verfahren zur katalytischen Herstellung von Kondensationsprodukten des Formaldehyds
JP6155187B2 (ja)	2010-03-30	2017-06-28	ヴァーセオンコーポレイション	トロンビンの阻害剤としての多置換芳香族化合物
WO2014145986A1 (en)	2013-03-15	2014-09-18	Verseon, Inc.	Multisubstituted aromatic compounds as serine protease inhibitors
ES2791749T3 (es)	2013-03-15	2020-11-05	Verseon Corp	Halogenopirazoles como inhibidores de la trombina
KR20170048410A (ko)	2014-09-17	2017-05-08	베르선 코포레이션	세린 프로테아제 저해제로서의 피라졸릴-치환된 피리돈 화합물
AU2016224974B2 (en)	2015-02-27	2019-09-26	Verseon Corporation	Substituted pyrazole compounds as serine protease inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT78388B (en) *	1983-04-12	1986-09-15	Smithkline Beckman Corp	Dopamine-beta-hydroxylase inhibitors
US4628059A (en) *	1985-10-31	1986-12-09	Smithklein Beckman Corporation	Dopamine-β-hydroxylase inhibitors

1987
- 1987-05-15 PH PH35265A patent/PH23506A/en unknown
- 1987-05-15 IL IL82542A patent/IL82542A0/xx unknown
- 1987-05-18 DK DK251087A patent/DK251087A/da not_active Application Discontinuation
- 1987-05-18 ZW ZW90/87A patent/ZW9087A1/xx unknown
- 1987-05-18 NZ NZ220347A patent/NZ220347A/xx unknown
- 1987-05-19 NO NO872094A patent/NO872094L/no unknown
- 1987-05-19 PT PT84904A patent/PT84904B/pt unknown
- 1987-05-20 EP EP87304504A patent/EP0246888A3/de not_active Withdrawn
- 1987-05-20 JP JP62123585A patent/JPS62283967A/ja active Pending
- 1987-05-21 HU HU872280A patent/HU201530B/hu not_active IP Right Cessation
- 1987-05-21 FI FI872249A patent/FI872249L/fi not_active Application Discontinuation
- 1987-05-21 ZA ZA873653A patent/ZA873653B/xx unknown
- 1987-05-22 KR KR870005065A patent/KR870011109A/ko not_active Withdrawn
- 1987-05-22 AU AU73344/87A patent/AU7334487A/en not_active Abandoned
- 1987-05-22 CN CN198787103808A patent/CN87103808A/zh active Pending

Also Published As

Publication number	Publication date
ZW9087A1 (en)	1987-09-02
PH23506A (en)	1989-08-16
HUT47920A (en)	1989-04-28
IL82542A0 (en)	1987-11-30
NO872094D0 (no)	1987-05-19
FI872249A7 (fi)	1987-11-24
NZ220347A (en)	1990-05-28
DK251087A (da)	1987-11-24
AU7334487A (en)	1987-11-26
JPS62283967A (ja)	1987-12-09
CN87103808A (zh)	1987-12-09
ZA873653B (en)	1988-08-31
HU201530B (en)	1990-11-28
FI872249A0 (fi)	1987-05-21
EP0246888A2 (de)	1987-11-25
DK251087D0 (da)	1987-05-18
PT84904B (en)	1989-07-17
KR870011109A (ko)	1987-12-21
EP0246888A3 (de)	1988-09-28
FI872249L (fi)	1987-11-24
PT84904A (en)	1987-06-01

Publication	Publication Date	Title
US4532331A (en)	1985-07-30	1-Benzyl-2-aminomethyl imidazole derivatives
SU1277894A3 (ru)	1986-12-15	Способ получени 3-/1-имидазолилалкил/индолов или их фармацевтически приемлемых кислотно-аддитивных солей
CS249544B2 (en)	1987-03-12	Method of new imidazolylphenylamidines production
US4798843A (en)	1989-01-17	2-mercaproimidazole dopamine-β-hydroxylase inhibitors
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