SK38599A3 - Derivates of piperidine-ketocarboxylic acid, their preparation and use - Google Patents

Derivates of piperidine-ketocarboxylic acid, their preparation and use Download PDF

Info

Publication number: SK38599A3
Authority: SK; Slovakia
Prior art keywords: alkyl; piperidine; phenyl; general formula; treatment
Prior art date: 1996-10-15

Application number

SK385-99A

Other languages

English (en)

Slovak (sk)

Inventor

Wilfried Lubisch

Achim Moller

Jurgen Delzer

Original Assignee

Basf 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.)

1996-10-15

Filing date

1997-09-23

Publication date

2000-04-10

1997-09-23 Application filed by Basf Ag filed Critical Basf Ag

2000-04-10 Publication of SK38599A3 publication Critical patent/SK38599A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
239000002253 acid Substances 0.000 title claims description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 22
150000001875 compounds Chemical class 0.000 claims abstract description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 11
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
239000003112 inhibitor Substances 0.000 claims description 25
108010032088 Calpain Proteins 0.000 claims description 24
102000007590 Calpain Human genes 0.000 claims description 24
-1 CF 3 Inorganic materials 0.000 claims description 14
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
102000005927 Cysteine Proteases Human genes 0.000 claims description 11
108010005843 Cysteine Proteases Proteins 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
208000028867 ischemia Diseases 0.000 claims description 5
230000004770 neurodegeneration Effects 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
230000006378 damage Effects 0.000 claims description 4
208000014674 injury Diseases 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
229930192474 thiophene Chemical group 0.000 claims description 4
230000008733 trauma Effects 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000002177 Cataract Diseases 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 3
230000003683 cardiac damage Effects 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
208000023105 Huntington disease Diseases 0.000 claims description 2
102000000589 Interleukin-1 Human genes 0.000 claims description 2
108010002352 Interleukin-1 Proteins 0.000 claims description 2
206010027476 Metastases Diseases 0.000 claims description 2
208000029549 Muscle injury Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
206010063897 Renal ischaemia Diseases 0.000 claims description 2
208000025747 Rheumatic disease Diseases 0.000 claims description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
206010047163 Vasospasm Diseases 0.000 claims description 2
238000002399 angioplasty Methods 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
210000004204 blood vessel Anatomy 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000004663 cell proliferation Effects 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
208000001286 intracranial vasospasm Diseases 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
210000002027 skeletal muscle Anatomy 0.000 claims description 2
210000000329 smooth muscle myocyte Anatomy 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
239000003814 drug Substances 0.000 claims 5
230000003961 neuronal insult Effects 0.000 claims 2
206010019196 Head injury Diseases 0.000 claims 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
208000006011 Stroke Diseases 0.000 claims 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
230000000740 bleeding effect Effects 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
238000007912 intraperitoneal administration Methods 0.000 claims 1
210000003205 muscle Anatomy 0.000 claims 1
208000031225 myocardial ischemia Diseases 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
229940126534 drug product Drugs 0.000 abstract 1
239000000047 product Substances 0.000 description 42
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 24
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 20
239000000203 mixture Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
108010079785 calpain inhibitors Proteins 0.000 description 13
210000004027 cell Anatomy 0.000 description 13
230000002829 reductive effect Effects 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
150000002576 ketones Chemical class 0.000 description 11
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
150000001408 amides Chemical class 0.000 description 10
239000011575 calcium Substances 0.000 description 10
229910052791 calcium Inorganic materials 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 9
125000004494 ethyl ester group Chemical group 0.000 description 8
108090000765 processed proteins & peptides Proteins 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000000872 buffer Substances 0.000 description 6
230000030833 cell death Effects 0.000 description 6
235000018102 proteins Nutrition 0.000 description 6
102000004169 proteins and genes Human genes 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
229940088598 enzyme Drugs 0.000 description 5
230000007017 scission Effects 0.000 description 5
239000000758 substrate Substances 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
238000003556 assay Methods 0.000 description 4
229930195712 glutamate Natural products 0.000 description 4
230000002427 irreversible effect Effects 0.000 description 4
150000004797 ketoamides Chemical class 0.000 description 4
125000000468 ketone group Chemical group 0.000 description 4
229950009215 phenylbutanoic acid Drugs 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
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230000000236 ionophoric effect Effects 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
125000005322 morpholin-1-yl group Chemical group 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical class OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
108010044467 Isoenzymes Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
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238000006859 Swern oxidation reaction Methods 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910001424 calcium ion Inorganic materials 0.000 description 2
HIYAVKIYRIFSCZ-UHFFFAOYSA-N calcium ionophore A23187 Natural products N=1C2=C(C(O)=O)C(NC)=CC=C2OC=1CC(C(CC1)C)OC1(C(CC1C)C)OC1C(C)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
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230000015556 catabolic process Effects 0.000 description 2
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GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 description 2
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SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 2
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WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
VJOKQRCHYVNKKH-UHFFFAOYSA-N 1-(naphthalene-2-carbonyl)piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)C1=CC=C(C=CC=C2)C2=C1 VJOKQRCHYVNKKH-UHFFFAOYSA-N 0.000 description 1
MDJITYWHEVEXJY-UHFFFAOYSA-N 1-naphthalen-2-ylsulfonylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 MDJITYWHEVEXJY-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Psychology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

SK385-99A 1996-10-15 1997-09-23 Derivates of piperidine-ketocarboxylic acid, their preparation and use SK38599A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19642591A DE19642591A1 (de)	1996-10-15	1996-10-15	Neue Piperidin-Ketocarbonsäure-Derivate, deren Herstellung und Anwendung
PCT/EP1997/005202 WO1998016512A1 (de)	1996-10-15	1997-09-23	Neue piperidin-ketocarbonsäure-derivate, deren herstellung und anwendung

Publications (1)

Publication Number	Publication Date
SK38599A3 true SK38599A3 (en)	2000-04-10

Family

ID=7808858

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK385-99A SK38599A3 (en)	1996-10-15	1997-09-23	Derivates of piperidine-ketocarboxylic acid, their preparation and use

Country Status (24)

Country	Link
US (1)	US6380220B1 (xx)
EP (1)	EP0934273A1 (xx)
JP (1)	JP2001501955A (xx)
KR (1)	KR20000049130A (xx)
CN (1)	CN1239950A (xx)
AR (1)	AR009379A1 (xx)
AU (1)	AU736754B2 (xx)
BG (1)	BG103338A (xx)
BR (1)	BR9711908A (xx)
CA (1)	CA2268917A1 (xx)
CO (1)	CO4930264A1 (xx)
CZ (1)	CZ126899A3 (xx)
DE (1)	DE19642591A1 (xx)
HR (1)	HRP970549A2 (xx)
HU (1)	HUP9904104A3 (xx)
IL (1)	IL129089A0 (xx)
NO (1)	NO991761L (xx)
NZ (1)	NZ334979A (xx)
PL (1)	PL332720A1 (xx)
RU (1)	RU2189974C2 (xx)
SK (1)	SK38599A3 (xx)
TR (1)	TR199900819T2 (xx)
WO (1)	WO1998016512A1 (xx)
ZA (1)	ZA979175B (xx)

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1996
- 1996-10-15 DE DE19642591A patent/DE19642591A1/de not_active Withdrawn
1997
- 1997-09-23 HU HU9904104A patent/HUP9904104A3/hu unknown
- 1997-09-23 CN CN97180507A patent/CN1239950A/zh active Pending
- 1997-09-23 US US09/284,543 patent/US6380220B1/en not_active Expired - Fee Related
- 1997-09-23 RU RU99109969/04A patent/RU2189974C2/ru active
- 1997-09-23 IL IL12908997A patent/IL129089A0/xx unknown
- 1997-09-23 JP JP10517955A patent/JP2001501955A/ja active Pending
- 1997-09-23 TR TR1999/00819T patent/TR199900819T2/xx unknown
- 1997-09-23 SK SK385-99A patent/SK38599A3/sk unknown
- 1997-09-23 CA CA002268917A patent/CA2268917A1/en not_active Abandoned
- 1997-09-23 BR BR9711908A patent/BR9711908A/pt unknown
- 1997-09-23 EP EP97910332A patent/EP0934273A1/de not_active Withdrawn
- 1997-09-23 KR KR1019990703216A patent/KR20000049130A/ko not_active Withdrawn
- 1997-09-23 NZ NZ334979A patent/NZ334979A/en unknown
- 1997-09-23 PL PL97332720A patent/PL332720A1/xx unknown
- 1997-09-23 WO PCT/EP1997/005202 patent/WO1998016512A1/de not_active Ceased
- 1997-09-23 AU AU47770/97A patent/AU736754B2/en not_active Ceased
- 1997-09-23 CZ CZ991268A patent/CZ126899A3/cs unknown
- 1997-10-14 CO CO97060053A patent/CO4930264A1/es unknown
- 1997-10-14 ZA ZA979175A patent/ZA979175B/xx unknown
- 1997-10-14 AR ARP970104718A patent/AR009379A1/es not_active Application Discontinuation
- 1997-10-14 HR HR19642591,3A patent/HRP970549A2/hr not_active Application Discontinuation
1999
- 1999-04-14 NO NO991761A patent/NO991761L/no not_active Application Discontinuation
- 1999-04-15 BG BG103338A patent/BG103338A/bg unknown

Also Published As

Publication number	Publication date
DE19642591A1 (de)	1998-04-16
CO4930264A1 (es)	2000-06-27
CA2268917A1 (en)	1998-04-23
PL332720A1 (en)	1999-10-11
AU736754B2 (en)	2001-08-02
WO1998016512A1 (de)	1998-04-23
KR20000049130A (ko)	2000-07-25
HUP9904104A3 (en)	2001-01-29
HUP9904104A2 (hu)	2000-05-28
AR009379A1 (es)	2000-04-12
NZ334979A (en)	2001-02-23
TR199900819T2 (xx)	1999-06-21
NO991761D0 (no)	1999-04-14
BG103338A (bg)	2000-01-31
IL129089A0 (en)	2000-02-17
ZA979175B (en)	1999-04-14
NO991761L (no)	1999-04-14
AU4777097A (en)	1998-05-11
HRP970549A2 (en)	1998-08-31
BR9711908A (pt)	1999-08-24
US6380220B1 (en)	2002-04-30
CN1239950A (zh)	1999-12-29
CZ126899A3 (cs)	1999-07-14
RU2189974C2 (ru)	2002-09-27
EP0934273A1 (de)	1999-08-11
JP2001501955A (ja)	2001-02-13

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