SK282953B6 - Hydroxylamínové deriváty a spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Hydroxylamínové deriváty a spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK282953B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; alkyl; defined above; piperidine
Prior art date: 1995-06-15

Application number

SK1713-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK171397A3 (en

Inventor

L�Szl� �R�Gdi

Ede M�Rv�Nyos

Mih�Ly Barab�S

L�Szl� Jaszlits

Katalin B�R�

Andrea Jedn�Kovits

Heged�S Erzs�Bet Radv�Nyn�

M�Ria K�Rthy

Nagy Istv�Nn� Udvardy

Original Assignee

Biorex Kutat� �S Fejleszt� Rt.

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.)

1995-06-15

Filing date

1996-06-14

Publication date

2003-01-09

1996-06-14 Application filed by Biorex Kutat� �S Fejleszt� Rt. filed Critical Biorex Kutat� �S Fejleszt� Rt.

1998-06-03 Publication of SK171397A3 publication Critical patent/SK171397A3/sk

2003-01-09 Publication of SK282953B6 publication Critical patent/SK282953B6/sk

Links

150000002443 hydroxylamines Chemical class 0.000 title claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
230000002253 anti-ischaemic effect Effects 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 90
150000003839 salts Chemical class 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims abstract description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 132
125000000217 alkyl group Chemical group 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
150000003053 piperidines Chemical class 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 29
238000005160 1H NMR spectroscopy Methods 0.000 description 27
238000003756 stirring Methods 0.000 description 23
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 22
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 16
101150065749 Churc1 gene Proteins 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
102100038239 Protein Churchill Human genes 0.000 description 16
-1 tert Chemical group 0.000 description 15
238000004440 column chromatography Methods 0.000 description 14
ZDWMZIWWYSLIQL-UHFFFAOYSA-N 1-aminooxy-3-piperidin-1-ylpropan-2-ol Chemical compound NOCC(O)CN1CCCCC1 ZDWMZIWWYSLIQL-UHFFFAOYSA-N 0.000 description 13
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000010410 layer Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
235000013877 carbamide Nutrition 0.000 description 5
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000010410 reperfusion Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
HVUAHWLBZZDJBA-UHFFFAOYSA-N 1-cyclohexyl-3-(2-hydroxy-3-piperidin-1-ylpropoxy)urea Chemical compound C1CCCCN1CC(O)CONC(=O)NC1CCCCC1 HVUAHWLBZZDJBA-UHFFFAOYSA-N 0.000 description 2
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 2
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
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 2
210000004351 coronary vessel Anatomy 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
MZNXUBVGQOSWEJ-UHFFFAOYSA-N o-(3-piperidin-1-ylpropyl)hydroxylamine Chemical compound NOCCCN1CCCCC1 MZNXUBVGQOSWEJ-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
ZNSIOEUWGZNHAQ-UHFFFAOYSA-N (3e)-n-diazoniopyridine-3-carboximidate Chemical compound [N-]=[N+]=NC(=O)C1=CC=CN=C1 ZNSIOEUWGZNHAQ-UHFFFAOYSA-N 0.000 description 1
ZWVLPNMFUGUUFL-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-hexyl-3-(2-hydroxy-3-morpholin-4-ylpropoxy)urea Chemical compound OC(=O)\C=C/C(O)=O.CCCCCCNC(=O)NOCC(O)CN1CCOCC1 ZWVLPNMFUGUUFL-BTJKTKAUSA-N 0.000 description 1
VARMSCKDCKYQRC-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NOCC(O)CN1CCCCC1 VARMSCKDCKYQRC-UHFFFAOYSA-N 0.000 description 1
PITPTOAZHDTGBI-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1CCCCN1CC(O)CONC(=O)NC1=CC=CC(C(F)(F)F)=C1 PITPTOAZHDTGBI-UHFFFAOYSA-N 0.000 description 1
TYYDSBNHEIUYCI-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-methylurea Chemical compound CNC(=O)NOCC(O)CN1CCCCC1 TYYDSBNHEIUYCI-UHFFFAOYSA-N 0.000 description 1
KVEVZSKQVNJNQU-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-octylurea Chemical compound CCCCCCCCNC(=O)NOCC(O)CN1CCCCC1 KVEVZSKQVNJNQU-UHFFFAOYSA-N 0.000 description 1
VRZDSOHJDNFFKK-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-pentylurea Chemical compound CCCCCNC(=O)NOCC(O)CN1CCCCC1 VRZDSOHJDNFFKK-UHFFFAOYSA-N 0.000 description 1
LUUHIYMARNWZSN-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-phenylurea Chemical compound C1CCCCN1CC(O)CONC(=O)NC1=CC=CC=C1 LUUHIYMARNWZSN-UHFFFAOYSA-N 0.000 description 1
XAVCWJUKSUDMRD-UHFFFAOYSA-N 1-(2-hydroxy-3-piperidin-1-ylpropoxy)-3-pyridin-3-ylurea Chemical compound C1CCCCN1CC(O)CONC(=O)NC1=CC=CN=C1 XAVCWJUKSUDMRD-UHFFFAOYSA-N 0.000 description 1
DJIVTCAYNPBDMP-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(2-hydroxy-3-piperidin-1-ylpropoxy)urea Chemical compound C1CCCCN1CC(O)CONC(=O)NC1=CC=CC(Cl)=C1 DJIVTCAYNPBDMP-UHFFFAOYSA-N 0.000 description 1
JWYRPOYJRRHHIL-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)piperidine Chemical compound C1CCCCN1CC1CO1 JWYRPOYJRRHHIL-UHFFFAOYSA-N 0.000 description 1
NQSSADCEQNEAIG-UHFFFAOYSA-N 1-[3-(4-benzylpiperazin-1-yl)-2-hydroxypropoxy]-3-propan-2-ylurea;hydrochloride Chemical compound Cl.C1CN(CC(O)CONC(=O)NC(C)C)CCN1CC1=CC=CC=C1 NQSSADCEQNEAIG-UHFFFAOYSA-N 0.000 description 1
ZNEXGSNILGKCHV-UHFFFAOYSA-N 1-aminooxy-3-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(O)CON ZNEXGSNILGKCHV-UHFFFAOYSA-N 0.000 description 1
FWJGBYCRQUPGEP-UHFFFAOYSA-N 1-aminooxy-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)CON FWJGBYCRQUPGEP-UHFFFAOYSA-N 0.000 description 1
COSDEZTULDESEV-UHFFFAOYSA-N 1-aminooxy-3-morpholin-4-ylpropan-2-ol Chemical compound NOCC(O)CN1CCOCC1 COSDEZTULDESEV-UHFFFAOYSA-N 0.000 description 1
PRQIUUOWRMOICX-UHFFFAOYSA-N 1-benzyl-3-(2-hydroxy-3-piperidin-1-ylpropoxy)urea Chemical compound C1CCCCN1CC(O)CONC(=O)NCC1=CC=CC=C1 PRQIUUOWRMOICX-UHFFFAOYSA-N 0.000 description 1
HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
IGMZDGBNMCELOE-UHFFFAOYSA-N 1-chloro-3-piperidin-1-ylpropan-2-ol Chemical compound ClCC(O)CN1CCCCC1 IGMZDGBNMCELOE-UHFFFAOYSA-N 0.000 description 1
JFSLWHPERGCMOT-UHFFFAOYSA-N 1-heptyl-1-(2-hydroxy-3-piperidin-1-ylpropoxy)urea Chemical compound OC(CON(C(=O)N)CCCCCCC)CN1CCCCC1 JFSLWHPERGCMOT-UHFFFAOYSA-N 0.000 description 1
SMXUVJJTNZTLOW-UHFFFAOYSA-N 1-hexyl-3-(3-piperidin-1-ylpropoxy)urea Chemical compound CCCCCCNC(=O)NOCCCN1CCCCC1 SMXUVJJTNZTLOW-UHFFFAOYSA-N 0.000 description 1
GFFGYTMCNVMFAJ-UHFFFAOYSA-N 1-isocyanato-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=C=O)=C1 GFFGYTMCNVMFAJ-UHFFFAOYSA-N 0.000 description 1
FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
RFXBSYPBSRSQDU-UHFFFAOYSA-N 1-isocyanatoheptane Chemical compound CCCCCCCN=C=O RFXBSYPBSRSQDU-UHFFFAOYSA-N 0.000 description 1
DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
PBDXOXOTLLDQKT-UHFFFAOYSA-N 1-pentyl-3-(3-piperidin-1-ylpropoxy)urea Chemical compound CCCCCNC(=O)NOCCCN1CCCCC1 PBDXOXOTLLDQKT-UHFFFAOYSA-N 0.000 description 1
COKIUVVGPDHTCF-UHFFFAOYSA-N 1-tert-butyl-3-(2-hydroxy-3-piperidin-1-ylpropoxy)urea Chemical compound CC(C)(C)NC(=O)NOCC(O)CN1CCCCC1 COKIUVVGPDHTCF-UHFFFAOYSA-N 0.000 description 1
AJTXNJYRZDUWSD-UHFFFAOYSA-N 1-tert-butyl-3-cyclohexyl-1-[3-(cyclohexylcarbamoylamino)oxy-2-hydroxypropyl]urea Chemical compound C1CCCCC1NC(=O)N(C(C)(C)C)CC(O)CONC(=O)NC1CCCCC1 AJTXNJYRZDUWSD-UHFFFAOYSA-N 0.000 description 1
FDPSIHMSJLZBPX-UHFFFAOYSA-N 3-(2-hydroxy-3-piperidin-1-ylpropoxy)-1,1-diphenylurea Chemical compound C1CCCCN1CC(O)CONC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 FDPSIHMSJLZBPX-UHFFFAOYSA-N 0.000 description 1
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 1
NDBNMTKTDWXWIZ-UHFFFAOYSA-N C1CCN(C(C1)O)CCCON Chemical compound C1CCN(C(C1)O)CCCON NDBNMTKTDWXWIZ-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
XMXJFKVLHWYHQF-UHFFFAOYSA-N OC(CON)CN1CCCCC1.C(CCCCC)NC(=O)NOCC(CN1CCCCC1)O Chemical compound OC(CON)CN1CCCCC1.C(CCCCC)NC(=O)NOCC(CN1CCCCC1)O XMXJFKVLHWYHQF-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002744 anti-aggregatory effect Effects 0.000 description 1
210000002376 aorta thoracic Anatomy 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
PQBSPTAPCMSZAA-UHFFFAOYSA-N benzyl n-hydroxycarbamate Chemical compound ONC(=O)OCC1=CC=CC=C1 PQBSPTAPCMSZAA-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
229960004027 molsidomine Drugs 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
PJLHXSBKGRJXHA-UHFFFAOYSA-N n-ethylcarbamoyl chloride Chemical compound CCNC(Cl)=O PJLHXSBKGRJXHA-UHFFFAOYSA-N 0.000 description 1
125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
206010037844 rash Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
230000002883 vasorelaxation effect Effects 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- 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
- A61P9/06—Antiarrhythmics
- 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
- A61P9/10—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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)

SK1713-97A 1995-06-15 1996-06-14 Hydroxylamínové deriváty a spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie SK282953B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU9501756A HU218480B (hu)	1995-06-15	1995-06-15	Hidroxilaminszármazékok, eljárás előállításukra és a vegyületeket tartalmazó gyógyszerkészítmények
PCT/HU1996/000033 WO1997000251A1 (en)	1995-06-15	1996-06-14	Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions

Publications (2)

Publication Number	Publication Date
SK171397A3 SK171397A3 (en)	1998-06-03
SK282953B6 true SK282953B6 (sk)	2003-01-09

Family

ID=10986948

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1713-97A SK282953B6 (sk)	1995-06-15	1996-06-14	Hydroxylamínové deriváty a spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (23)

Country	Link
US (1)	US6002002A (da)
EP (1)	EP0832079B1 (da)
JP (1)	JP4083800B2 (da)
KR (1)	KR100444780B1 (da)
AT (1)	ATE215075T1 (da)
AU (1)	AU703163B2 (da)
BR (1)	BR9608929A (da)
CA (1)	CA2221689C (da)
CZ (1)	CZ295547B6 (da)
DE (1)	DE69620175T2 (da)
DK (1)	DK0832079T3 (da)
ES (1)	ES2174077T3 (da)
HR (1)	HRP960279B1 (da)
HU (1)	HU218480B (da)
IL (1)	IL122141A (da)
IN (1)	IN185781B (da)
PL (1)	PL185592B1 (da)
PT (1)	PT832079E (da)
SI (1)	SI0832079T1 (da)
SK (1)	SK282953B6 (da)
WO (1)	WO1997000251A1 (da)
YU (1)	YU49419B (da)
ZA (1)	ZA964978B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA64716C2 (en) *	1996-08-09	2004-03-15		Pharmaceuticals for therapy or prevention of illnesses connected with dysfunction of vascular endothelial cells
MXPA02008111A (es) *	2000-02-21	2002-11-29	Astrazeneca Ab	N-hidroxiformamidas substituidas con piperidina y piperazina como inhibidores de metaloproteinasas.
CA2471752A1 (en)	2002-01-11	2003-07-17	Biorex Kutato Es Fejlesztoe Rt.	Carboxamidine derivatives and their use in the treatment of vascular diseases
US7943567B2 (en)	2004-01-30	2011-05-17	E.I. Du Pont De Nemours And Company	Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
US8318656B2 (en)	2007-07-03	2012-11-27	E. I. Du Pont De Nemours And Company	Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
KR101405103B1 (ko) *	2014-03-25	2014-06-10	재 남 우	레버식 수동개방기구를 구비하는 초고압 압축가스 개폐장치

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE369944C (de) *	1918-03-07	1923-02-24	Anilin Fabrikation Ag	Verfahren zur Darstellung von Tetrahydronaphthalin
DE2651083A1 (de) *	1976-11-09	1978-05-18	Hoechst Ag	Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung
EP0369944A1 (de) *	1988-11-18	1990-05-23	Ciba-Geigy Ag	Substituierte Oxadiaminobutane
EP0495750A3 (en) *	1991-01-14	1992-09-16	Ciba-Geigy Ag	Heterocyclic hydroxylamine

1995
- 1995-06-15 HU HU9501756A patent/HU218480B/hu not_active IP Right Cessation
1996
- 1996-06-12 IN IN1286DE1996 patent/IN185781B/en unknown
- 1996-06-12 HR HR960279A patent/HRP960279B1/xx not_active IP Right Cessation
- 1996-06-12 ZA ZA9604978A patent/ZA964978B/xx unknown
- 1996-06-14 CZ CZ19974015A patent/CZ295547B6/cs not_active IP Right Cessation
- 1996-06-14 IL IL12214196A patent/IL122141A/xx not_active IP Right Cessation
- 1996-06-14 BR BR9608929A patent/BR9608929A/pt active Search and Examination
- 1996-06-14 SI SI9630462T patent/SI0832079T1/xx unknown
- 1996-06-14 AT AT96921009T patent/ATE215075T1/de not_active IP Right Cessation
- 1996-06-14 CA CA002221689A patent/CA2221689C/en not_active Expired - Fee Related
- 1996-06-14 AU AU62376/96A patent/AU703163B2/en not_active Ceased
- 1996-06-14 US US08/914,115 patent/US6002002A/en not_active Expired - Fee Related
- 1996-06-14 YU YU36996A patent/YU49419B/sh unknown
- 1996-06-14 ES ES96921009T patent/ES2174077T3/es not_active Expired - Lifetime
- 1996-06-14 PT PT96921009T patent/PT832079E/pt unknown
- 1996-06-14 EP EP96921009A patent/EP0832079B1/en not_active Expired - Lifetime
- 1996-06-14 KR KR1019970709431A patent/KR100444780B1/ko not_active Expired - Fee Related
- 1996-06-14 JP JP50282997A patent/JP4083800B2/ja not_active Expired - Fee Related
- 1996-06-14 DE DE69620175T patent/DE69620175T2/de not_active Expired - Fee Related
- 1996-06-14 SK SK1713-97A patent/SK282953B6/sk not_active IP Right Cessation
- 1996-06-14 PL PL96324197A patent/PL185592B1/pl not_active IP Right Cessation
- 1996-06-14 DK DK96921009T patent/DK0832079T3/da active
- 1996-06-14 WO PCT/HU1996/000033 patent/WO1997000251A1/en not_active Ceased

Also Published As

Publication number	Publication date
CA2221689C (en)	2007-08-07
SI0832079T1 (en)	2002-08-31
PL324197A1 (en)	1998-05-11
BR9608929A (pt)	1999-06-15
US6002002A (en)	1999-12-14
PT832079E (pt)	2002-07-31
WO1997000251A1 (en)	1997-01-03
HRP960279B1 (en)	2002-02-28
KR100444780B1 (ko)	2004-11-26
IL122141A (en)	2003-07-06
DE69620175D1 (de)	2002-05-02
YU49419B (sh)	2006-01-16
HRP960279A2 (en)	1997-12-31
JP4083800B2 (ja)	2008-04-30
ES2174077T3 (es)	2002-11-01
HU9501756D0 (en)	1995-08-28
AU703163B2 (en)	1999-03-18
CA2221689A1 (en)	1997-01-03
IL122141A0 (en)	1998-04-05
HUT74621A (en)	1997-01-28
DE69620175T2 (de)	2002-08-22
CZ401597A3 (cs)	1998-04-15
PL185592B1 (pl)	2003-06-30
KR19990022961A (ko)	1999-03-25
MX9710172A (es)	1998-07-31
EP0832079B1 (en)	2002-03-27
DK0832079T3 (da)	2002-06-03
SK171397A3 (en)	1998-06-03
ZA964978B (en)	1997-02-24
HU218480B (hu)	2000-09-28
CZ295547B6 (cs)	2005-08-17
IN185781B (da)	2001-04-28
AU6237696A (en)	1997-01-15
YU36996A (sh)	1998-11-05
JPH11507662A (ja)	1999-07-06
ATE215075T1 (de)	2002-04-15
EP0832079A1 (en)	1998-04-01

Legal Events

Date	Code	Title	Description
2010-03-08	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20090614

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