LV10097B - New pharmacologically active catechol derivatives - Google Patents

New pharmacologically active catechol derivatives Download PDF

Info

Publication number: LV10097B
Authority: LV; Latvia
Prior art keywords: formula; dihydroxy; group; compound; sulfur
Prior art date: 1990-04-27

Application number

LVP-92-185A

Other languages

English (en)

Latvian (lv)

Other versions

LV10097A (lv

Inventor

Reijo Johannes B Ckstrim

Erkki Juhani Honkanen

Inge-Britt Yvonne Linden

Erkki Aarne Olavi Nissinen

Aino Kyllikki Pippuri

Pentti Pohto

Tapio Korkolainen

Original Assignee

Orion Yhtym Oy

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.)

1990-04-27

Filing date

1992-10-26

Publication date

1995-02-20

1990-04-27 Priority claimed from GB909009565A external-priority patent/GB9009565D0/en

1991-01-24 Priority claimed from GB919101563A external-priority patent/GB9101563D0/en

1992-10-26 Application filed by Orion Yhtym Oy filed Critical Orion Yhtym Oy

1994-05-10 Publication of LV10097A publication Critical patent/LV10097A/xx

1995-02-20 Publication of LV10097B publication Critical patent/LV10097B/en

Links

150000005206 1,2-dihydroxybenzenes Chemical class 0.000 title abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
239000001301 oxygen Substances 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 53
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
239000011593 sulfur Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
-1 3,4-dihydroxy-5-nitrophenyl Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
RTDXEFCIOVRBTK-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=S)N2)=O)=C1 RTDXEFCIOVRBTK-UHFFFAOYSA-N 0.000 claims description 4
HOJYNCFNHMKMME-UHFFFAOYSA-N 5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one Chemical compound ClC1=C(O)C(O)=CC(C=C2C(NC(=S)N2)=O)=C1 HOJYNCFNHMKMME-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 2
239000013543 active substance Substances 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 2
201000011510 cancer Diseases 0.000 abstract description 2
230000005779 cell damage Effects 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 abstract description 2
208000019622 heart disease Diseases 0.000 abstract description 2
208000027866 inflammatory disease Diseases 0.000 abstract description 2
206010039073 rheumatoid arthritis Diseases 0.000 abstract description 2
206010052779 Transplant rejections Diseases 0.000 abstract 1
208000028867 ischemia Diseases 0.000 abstract 1
239000008046 pharmaceutical antioxidant Substances 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
BBFJODMCHICIAA-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC([N+]([O-])=O)=C1O BBFJODMCHICIAA-UHFFFAOYSA-N 0.000 description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
DYYFMMDEOYTQBR-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-1,3-diazinane-2,4,6-trione Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=O)NC2=O)=O)=C1 DYYFMMDEOYTQBR-UHFFFAOYSA-N 0.000 description 6
UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical class O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
DVCPMGUHULGJKB-UHFFFAOYSA-N 2,3-dihydroxy-5-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzonitrile Chemical compound N#CC1=C(O)C(O)=CC(C=C2C(NC(=S)S2)=O)=C1 DVCPMGUHULGJKB-UHFFFAOYSA-N 0.000 description 3
GXFQIZZABFLIEU-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=S)S2)=O)=C1 GXFQIZZABFLIEU-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical class O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical class O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
VGGLJAAAJABETC-UHFFFAOYSA-N 2,3-dihydroxy-5-[(5-oxo-2-sulfanylideneimidazolidin-4-ylidene)methyl]benzonitrile Chemical compound N#CC1=C(O)C(O)=CC(C=C2C(NC(=S)N2)=O)=C1 VGGLJAAAJABETC-UHFFFAOYSA-N 0.000 description 2
LRIYFYUQOIQGQV-UHFFFAOYSA-N 2-amino-1,3-thiazolidin-4-one Chemical group NC1NC(=O)CS1 LRIYFYUQOIQGQV-UHFFFAOYSA-N 0.000 description 2
VOZATWIWYQFWAU-UHFFFAOYSA-N 2-amino-5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidin-4-one Chemical group S1C(N)NC(=O)C1=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 VOZATWIWYQFWAU-UHFFFAOYSA-N 0.000 description 2
JKLZCQWVERBDEZ-UHFFFAOYSA-N 3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical class CN1C(=O)CSC1=S JKLZCQWVERBDEZ-UHFFFAOYSA-N 0.000 description 2
IFXJQJKDPAJVMO-UHFFFAOYSA-N 4-sulfanylidene-1,3-oxazolidin-2-one Chemical class O=C1NC(=S)CO1 IFXJQJKDPAJVMO-UHFFFAOYSA-N 0.000 description 2
SJDZPXVXVOOLDY-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=O)S2)=O)=C1 SJDZPXVXVOOLDY-UHFFFAOYSA-N 0.000 description 2
HAUHOYNOGDYSMO-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound O=C1N(C)C(=S)SC1=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 HAUHOYNOGDYSMO-UHFFFAOYSA-N 0.000 description 2
DOZYMDSFEVWFEQ-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=O)N2)=O)=C1 DOZYMDSFEVWFEQ-UHFFFAOYSA-N 0.000 description 2
LFEDCJVVFSXHIK-UHFFFAOYSA-N 5-[(3-chloro-4,5-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound ClC1=C(O)C(O)=CC(C=C2C(NC(=O)S2)=O)=C1 LFEDCJVVFSXHIK-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
241000282414 Homo sapiens Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000003859 lipid peroxidation Effects 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical group NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical class O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
XTSVDOIDJDJMDS-UHFFFAOYSA-N 4-sulfanylidene-1,3-thiazolidin-2-one Chemical compound O=C1NC(=S)CS1 XTSVDOIDJDJMDS-UHFFFAOYSA-N 0.000 description 1
HUYDMMMUORAMHU-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-4-sulfanylidene-1,3-oxazolidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=O)O2)=S)=C1 HUYDMMMUORAMHU-UHFFFAOYSA-N 0.000 description 1
JPSVKWPZYPKOEK-UHFFFAOYSA-N 5-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=C2C(NC(=O)S2)=S)=C1 JPSVKWPZYPKOEK-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-AKLPVKDBSA-N Sulfur-35 Chemical compound [35S] NINIDFKCEFEMDL-AKLPVKDBSA-N 0.000 description 1
230000032683 aging Effects 0.000 description 1
239000003288 aldose reductase inhibitor Substances 0.000 description 1
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001378 electrochemiluminescence detection Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
229940097156 peroxyl Drugs 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003712 vitamin E derivatives Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/46—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Toxicology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Transplantation (AREA)
Biochemistry (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

LVP-92-185A 1990-04-27 1992-10-26 New pharmacologically active catechol derivatives LV10097B (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB909009565A GB9009565D0 (en)	1990-04-27	1990-04-27	New pharmacologically active catechol derivatives
GB919101563A GB9101563D0 (en)	1991-01-24	1991-01-24	New pharmacologically active catechol derivatives
PCT/FI1991/000124 WO1991017151A1 (fr)	1990-04-27	1991-04-26	Nouveaux derives de pyrocatechine a activite pharmacologique

Publications (2)

Publication Number	Publication Date
LV10097A LV10097A (lv)	1994-05-10
LV10097B true LV10097B (en)	1995-02-20

Family

ID=26297011

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-92-185A LV10097B (en)	1990-04-27	1992-10-26	New pharmacologically active catechol derivatives

Country Status (17)

Country	Link
US (3)	US5362733A (fr)
EP (1)	EP0526598B1 (fr)
JP (1)	JP2972377B2 (fr)
KR (1)	KR100207144B1 (fr)
AT (1)	ATE146462T1 (fr)
AU (1)	AU646464B2 (fr)
CA (1)	CA2080917C (fr)
DE (1)	DE69123738T2 (fr)
FI (1)	FI95129C (fr)
HU (1)	HU214872B (fr)
IE (1)	IE911430A1 (fr)
LT (1)	LT3137B (fr)
LV (1)	LV10097B (fr)
NO (1)	NO301928B1 (fr)
PL (1)	PL166269B1 (fr)
PT (1)	PT97507B (fr)
WO (1)	WO1991017151A1 (fr)

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EP0722729A3 (fr) *	1995-01-23	1997-11-26	Eli Lilly And Company	Rhodanines aryl-substituées pour le traitement de la sclérose multiple
WO1998033777A1 (fr) *	1997-01-31	1998-08-06	Shionogi & Co., Ltd.	Composes ayant une activite inhibant la metalloprotease
JP2001514663A (ja) *	1997-03-12	2001-09-11	エスモンド，ロバートダブリュー．	アルツハイマー病を処置または予防するための方法
US20040058873A1 (en) *	1998-03-12	2004-03-25	Esmond Robert W.	Method for treating or preventing Alzheimer's disease
US6191154B1 (en)	1998-11-27	2001-02-20	Case Western Reserve University	Compositions and methods for the treatment of Alzheimer's disease, central nervous system injury, and inflammatory diseases
AU7961800A (en) *	1999-10-28	2001-05-08	Kyowa Hakko Kogyo Co. Ltd.	Thiazolidinedione derivatives
WO2002053155A1 (fr) *	2000-12-30	2002-07-11	Geron Corporation	Inhibiteur de telomerase
WO2003009807A2 (fr) *	2001-07-23	2003-02-06	Galileo Laboratories, Inc.	Composes cytoprotecteurs, procedes et formulations pharmaceutiques et cosmetiques
US6679051B1 (en) *	2002-07-31	2004-01-20	Ford Global Technologies, Llc	Diesel engine system for use with emission control device
BRPI0416752B8 (pt)	2003-11-21	2021-05-25	Actelion Pharmaceuticals Ltd	composição farmacêutica, uso de um ou mais compostos, e, compostos
USRE43833E1 (en)	2003-11-21	2012-11-27	Actelion Pharmaceuticals Ltd.	Thiazolidin-4-one derivatives
US7872027B2 (en) *	2006-02-17	2011-01-18	University Of Pittsburgh - Of The Commonwealth System Of Higher Education	Low molecular weight Myc-max inhibitors
DK2094676T3 (da) *	2006-11-23	2013-06-10	Actelion Pharmaceuticals Ltd	Ny fremgangsmåde til fremstillingen af 2-iminothiazolidin-4-on-derivater
US8912340B2 (en)	2006-11-23	2014-12-16	Actelion Pharmaceuticals Ltd.	Process for the preparation of 2-imino-thiazolidin-4-one derivatives
FR2919608B1 (fr) *	2007-08-01	2012-10-05	Univ Rennes	Derives d'imidazolones,procede de preparation et applications biologiques
AU2009274571A1 (en) *	2008-07-23	2010-01-28	Massachusetts Institute Of Technology	Activation of histone deacetylase 1 (HDAC1) protects against DNA damage and increases neuronal survival
KR101411838B1 (ko) *	2011-02-09	2014-06-27	부산대학교 산학협력단	피부미백, 항산화 및 ｐｐａｒ 활성을 갖는 신규 화합물 및 이의 의학적 용도
PT2734510T (pt)	2011-07-22	2019-02-13	Massachusetts Inst Technology	Ativadores de histona desacetilases de classe i (hdacs) e seus usos
HUE050733T2 (hu)	2012-08-17	2021-01-28	Actelion Pharmaceuticals Ltd	Eljárás (2Z,5Z)-5-(3-klór-4-((R)-2,3-dihidroxipropoxi)benzilidén)-2-(pro-pilimino)-3-(O-tolil)tiazolidin-4-on elõállítására és ezen eljárásban alkalmazott köztitermék
DK3439667T3 (da)	2016-04-05	2024-04-02	Immune Sensor Llc	Cgas antagonist forbindelser
JPWO2022163843A1 (fr) *	2021-02-01	2022-08-04

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JPS60233063A (ja) *	1984-05-02	1985-11-19	Showa Denko Kk	５−ベンジリデンヒダントインの製造法
US4650876A (en) *	1984-08-17	1987-03-17	Stauffer Chemical Company	Hydrogenation of substituted, unsaturated hydantoins to substituted, saturated hydantoins
US4582903A (en) *	1984-08-17	1986-04-15	Stauffer Chemical Company	Synthesis of unsaturated hydantoins with an inexpensive catalyst
PT83152B (pt) *	1985-08-09	1989-03-30	Lilly Co Eli	Processo para a preparacao de compostos di-t-butilfenoicos
US5208250A (en) *	1988-05-25	1993-05-04	Warner-Lambert Company	Known and selected novel arylmethylenyl derivatives of thiazolidinones, imidazolidinones and oxazolidinones useful as antiallergy agents and anti-inflammatory agents
US5306822A (en) *	1988-05-25	1994-04-26	Warner-Lambert Company	Arylmethylenyl derivatives of oxazolidinone
IE940525L (en) *	1988-05-25	1989-11-25	Warner Lambert Co	Known and selected novel arylmethylenyl derivatives of¹thiazolidinones, imidazolidinones and oxazolidinones useful¹as antiallergy agents and antiinflammatory agents
GB8911073D0 (en) *	1989-05-15	1989-06-28	Fujisawa Pharmaceutical Co	New benzofuran derivatives,a process for the preparation thereof and pharmaceutical composition comprising the same
JPH1052765A (ja)	1996-08-09	1998-02-24	Sukematsu Iwashita	鉄筋材の圧接装置

1991
- 1991-04-26 CA CA002080917A patent/CA2080917C/fr not_active Expired - Fee Related
- 1991-04-26 HU HU9203369A patent/HU214872B/hu not_active IP Right Cessation
- 1991-04-26 EP EP91920959A patent/EP0526598B1/fr not_active Expired - Lifetime
- 1991-04-26 US US07/949,477 patent/US5362733A/en not_active Expired - Fee Related
- 1991-04-26 AU AU77618/91A patent/AU646464B2/en not_active Ceased
- 1991-04-26 AT AT91920959T patent/ATE146462T1/de not_active IP Right Cessation
- 1991-04-26 PT PT97507A patent/PT97507B/pt not_active IP Right Cessation
- 1991-04-26 PL PL91296620A patent/PL166269B1/pl unknown
- 1991-04-26 WO PCT/FI1991/000124 patent/WO1991017151A1/fr not_active Ceased
- 1991-04-26 DE DE69123738T patent/DE69123738T2/de not_active Expired - Fee Related
- 1991-04-26 JP JP3096814A patent/JP2972377B2/ja not_active Expired - Fee Related
- 1991-04-29 IE IE143091A patent/IE911430A1/en not_active IP Right Cessation
1992
- 1992-10-21 KR KR1019920702604A patent/KR100207144B1/ko not_active Expired - Fee Related
- 1992-10-23 FI FI924838A patent/FI95129C/fi active
- 1992-10-26 LV LVP-92-185A patent/LV10097B/en unknown
- 1992-10-26 NO NO924132A patent/NO301928B1/no not_active IP Right Cessation
- 1992-11-17 LT LTIP227A patent/LT3137B/lt not_active IP Right Cessation
1994
- 1994-10-18 US US08/325,024 patent/US5614541A/en not_active Expired - Fee Related
1995
- 1995-06-07 US US08/472,658 patent/US5889037A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HU214872B (hu)	1998-07-28
PL166269B1 (pl)	1995-04-28
NO301928B1 (no)	1997-12-29
KR100207144B1 (en)	1999-07-15
ATE146462T1 (de)	1997-01-15
US5362733A (en)	1994-11-08
FI924838A0 (fi)	1992-10-23
DE69123738D1 (en)	1997-01-30
PT97507A (pt)	1992-01-31
IE911430A1 (en)	1991-11-06
FI95129B (fi)	1995-09-15
FI95129C (fi)	1995-12-27
FI924838A7 (fi)	1992-10-23
HU9203369D0 (en)	1993-01-28
NO924132L (no)	1992-12-23
KR930700468A (ko)	1993-03-15
CA2080917A1 (fr)	1991-10-28
NO924132D0 (no)	1992-10-26
DE69123738T2 (de)	1997-07-03
AU646464B2 (en)	1994-02-24
EP0526598A1 (fr)	1993-02-10
CA2080917C (fr)	2001-06-12
JP2972377B2 (ja)	1999-11-08
US5614541A (en)	1997-03-25
US5889037A (en)	1999-03-30
JPH05331148A (ja)	1993-12-14
EP0526598B1 (fr)	1996-12-18
LV10097A (lv)	1994-05-10
AU7761891A (en)	1991-11-27
HUT65662A (en)	1994-07-28
PT97507B (pt)	1998-08-31
WO1991017151A1 (fr)	1991-11-14
LTIP227A (lt)	1994-08-25
LT3137B (en)	1995-01-31

Publication	Publication Date	Title
CA2080917C (fr)	2001-06-12	Derives pharmacologiquement actifs du catechol
IE83426B1 (en)		New pharmacologically active catechol derivatives
CA2073981C (fr)	2002-01-08	Derives de 2-arylthiazole et composition pharmaceutique a base de ces derives
US4552874A (en)	1985-11-12	Pyrazolooxazines, pyrazolothiazines, and pryazoloquinolines and their use as medicaments
US5336677A (en)	1994-08-09	Substituted aminopyrimidines as antihypertensives
US4785008A (en)	1988-11-15	N-substituted 2-amino-thiazoles, process for their preparation and their therapeutic application
US5008266A (en)	1991-04-16	4(3H)-quinazolinone derivatives and pharmaceutical compositions
HU208826B (en)	1994-01-28	Process for producing pteridin-4-/3h/-one derivatives and pharmaceutical compositions comprising such derivatives as active ingredient
US6121303A (en)	2000-09-19	Pharmacologically active catechol derivatives
US4397849A (en)	1983-08-09	Benzothiazine derivatives
RU2096407C1 (ru)	1997-11-20	Производные катехола и способ их получения
CA2377230C (fr)	2009-06-02	Composes de benzimidazole et medicaments les contenant
HRP921248A2 (en)	1998-08-31	New pharmacologically active catehol derivatives
BG61646B1 (bg)	1998-02-27	фармакологично активни катехинови съединения, метод за получаването им и тяхното използване
US5468761A (en)	1995-11-21	4-methyl-5-substituted-1,3-oxazoles having anti-inflammatory activity
SK279658B6 (sk)	1999-02-11	Katecholová zlúčenina, spôsob jej prípravy, farmac
IE54121B1 (en)	1989-06-21	Pharmaceutically active imidazolecarboxylic acid derivatives
RO109841B1 (ro)	1995-06-30	Derivați de catechol și procedeu de preparare a acestora
JPH03148269A (ja)	1991-06-25	ピペラジン誘導体及びこれを含有する肝疾患治療剤
TH79774A (th)	2006-09-07	ไบไซคลิคเฮเทอโรไซเคิลสำหรับการรักษาโรคเบาหวาน และโรคอื่น ๆ