DD297973A5 - Neue heterozyklische, stickstoff- und schwefelhaltige verbindungen, pharmazeutische zusammensetzungen, die dieselben enthalten und verfahren zu deren herstellung - Google Patents

Neue heterozyklische, stickstoff- und schwefelhaltige verbindungen, pharmazeutische zusammensetzungen, die dieselben enthalten und verfahren zu deren herstellung Download PDF

Info

Publication number: DD297973A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; formula; group; propan; thiazolidinyl
Prior art date: 1989-07-11

Application number

DD90342666A

Other languages

German (de)

English (en)

Inventor

Karoly Nador

Pal Scheiber

Erzsebet Szelecsenyi

Bela Molnar

Laszlo Szporny

Bela Kiss

Egon Karpati

Eva Palosi

Dora Groo

Istvan Laszlovszky

Zsolt Szombathelyi

Adam Sarkadi

Aniko Gere

Mihaly Bodo

Katalin Csomor

Judit Laszy

Zsolt Szentirmay

Original Assignee

��@��@��@��@��Kk��

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.)

1989-07-11

Filing date

1990-07-10

Publication date

1992-01-30

1990-07-10 Application filed by ��@��@��@��@��Kk�� filed Critical ��@��@��@��@��Kk��

1992-01-30 Publication of DD297973A5 publication Critical patent/DD297973A5/de

Links

150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 6
229910052757 nitrogen Inorganic materials 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title 1
150000003464 sulfur compounds Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 76
239000001257 hydrogen Substances 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
206010021143 Hypoxia Diseases 0.000 claims abstract description 14
150000002431 hydrogen Chemical group 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 claims abstract description 9
125000005059 halophenyl group Chemical group 0.000 claims abstract description 7
208000029028 brain injury Diseases 0.000 claims abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
208000002381 Brain Hypoxia Diseases 0.000 claims abstract description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
206010039966 Senile dementia Diseases 0.000 claims abstract description 4
125000005418 aryl aryl group Chemical group 0.000 claims abstract description 4
208000035475 disorder Diseases 0.000 claims abstract description 4
230000006870 function Effects 0.000 claims abstract description 3
230000008447 perception Effects 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
-1 ethylene carbonyl group Chemical group 0.000 claims description 43
238000002360 preparation method Methods 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
229930040373 Paraformaldehyde Natural products 0.000 claims description 24
229920002866 paraformaldehyde Polymers 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 22
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
239000000126 substance Substances 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
230000007954 hypoxia Effects 0.000 claims description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 7
150000002576 ketones Chemical class 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
239000001632 sodium acetate Substances 0.000 claims description 7
235000017281 sodium acetate Nutrition 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 4
206010012289 Dementia Diseases 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
MMCYYQAXCZXRSL-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCN1CSCC1 MMCYYQAXCZXRSL-UHFFFAOYSA-N 0.000 claims description 3
206010061216 Infarction Diseases 0.000 claims description 3
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
230000007574 infarction Effects 0.000 claims description 3
BTMNUJLKGRYDHA-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound C1=CC(Br)=CC=C1C(=O)CCN1CSCC1 BTMNUJLKGRYDHA-UHFFFAOYSA-N 0.000 claims description 2
SKOFTCJMNIJONB-UHFFFAOYSA-N 1-phenyl-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound C=1C=CC=CC=1C(=O)CCN1CCSC1 SKOFTCJMNIJONB-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
229920000180 alkyd Polymers 0.000 claims 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
IJMAIQBOEPHBND-UHFFFAOYSA-N 1-(4-bromophenyl)-2-methyl-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound C=1C=C(Br)C=CC=1C(=O)C(C)CN1CCSC1 IJMAIQBOEPHBND-UHFFFAOYSA-N 0.000 claims 1
BUIFSGLUCSZLHL-UHFFFAOYSA-N 1-(4-methoxy-2-methylphenyl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound CC1=CC(OC)=CC=C1C(=O)CCN1CSCC1 BUIFSGLUCSZLHL-UHFFFAOYSA-N 0.000 claims 1
DZPMSNLTPRFWES-UHFFFAOYSA-N 1-(4-phenylphenyl)-3-(1,3-thiazinan-3-yl)propan-1-one Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)CCN1CCCSC1 DZPMSNLTPRFWES-UHFFFAOYSA-N 0.000 claims 1
HSMVUXNSGFJFCS-UHFFFAOYSA-N 1-(5-chlorothiophen-2-yl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound S1C(Cl)=CC=C1C(=O)CCN1CSCC1 HSMVUXNSGFJFCS-UHFFFAOYSA-N 0.000 claims 1
JIGFWRVYDXSWHJ-UHFFFAOYSA-N 1-(5-ethylthiophen-2-yl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound S1C(CC)=CC=C1C(=O)CCN1CSCC1 JIGFWRVYDXSWHJ-UHFFFAOYSA-N 0.000 claims 1
SCKVFABDHRQHPB-UHFFFAOYSA-N 2-methyl-1-phenyl-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C)CN1CCSC1 SCKVFABDHRQHPB-UHFFFAOYSA-N 0.000 claims 1
DMMGWCHCDHMVSP-UHFFFAOYSA-N 3-(1,3-thiazolidin-3-yl)-1-thiophen-2-ylpropan-1-one Chemical compound C=1C=CSC=1C(=O)CCN1CCSC1 DMMGWCHCDHMVSP-UHFFFAOYSA-N 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
230000004064 dysfunction Effects 0.000 claims 1
RQJMVKIDEHGZEP-UHFFFAOYSA-N methyl 3-[3-(4-fluorophenyl)-3-oxopropyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylate Chemical compound C1SC(C)(C)C(C(=O)OC)N1CCC(=O)C1=CC=C(F)C=C1 RQJMVKIDEHGZEP-UHFFFAOYSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
230000000141 anti-hypoxic effect Effects 0.000 abstract description 9
230000002490 cerebral effect Effects 0.000 abstract description 4
125000003118 aryl group Chemical group 0.000 abstract description 3
201000010099 disease Diseases 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
230000006931 brain damage Effects 0.000 abstract 1
231100000874 brain damage Toxicity 0.000 abstract 1
230000001146 hypoxic effect Effects 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 116
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 36
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 28
239000000203 mixture Substances 0.000 description 26
239000000047 product Substances 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000001953 recrystallisation Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000002244 precipitate Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
230000004083 survival effect Effects 0.000 description 12
238000010992 reflux Methods 0.000 description 10
MPGQQQKGAXDBDN-UHFFFAOYSA-N 1,3-thiazolidin-3-ium;chloride Chemical compound Cl.C1CSCN1 MPGQQQKGAXDBDN-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
125000001255 4-fluorophenyl group Chemical class [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
206010002660 Anoxia Diseases 0.000 description 5
241000976983 Anoxia Species 0.000 description 5
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230000007953 anoxia Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
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XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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229940102223 injectable solution Drugs 0.000 description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
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230000000241 respiratory effect Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
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PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
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KTJRGPZVSKWRTJ-UHFFFAOYSA-N 3-chloro-1-phenylpropan-1-one Chemical compound ClCCC(=O)C1=CC=CC=C1 KTJRGPZVSKWRTJ-UHFFFAOYSA-N 0.000 description 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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230000003444 anaesthetic effect Effects 0.000 description 2
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
239000008298 dragée Substances 0.000 description 2
ZRBNETYZYOXTLS-UHFFFAOYSA-N ethyl 1,3-thiazolidine-4-carboxylate Chemical compound CCOC(=O)C1CSCN1 ZRBNETYZYOXTLS-UHFFFAOYSA-N 0.000 description 2
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LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
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DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
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ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
HOQOADCYROWGQA-UHFFFAOYSA-N 1,3-thiazinane Chemical class C1CNCSC1 HOQOADCYROWGQA-UHFFFAOYSA-N 0.000 description 1
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ODCNZDPMHZNSFR-UHFFFAOYSA-N 1,3-thiazolidine;hydrobromide Chemical compound Br.C1CSCN1 ODCNZDPMHZNSFR-UHFFFAOYSA-N 0.000 description 1
LPTXRCOSWDBBDP-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-(1,3-thiazolidin-3-yl)propan-1-one Chemical compound COC1=CC=CC(C(=O)CCN2CSCC2)=C1 LPTXRCOSWDBBDP-UHFFFAOYSA-N 0.000 description 1
BAYUSCHCCGXLAY-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(C)=O)=C1 BAYUSCHCCGXLAY-UHFFFAOYSA-N 0.000 description 1
WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A61P25/28—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
- 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
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Thiazole And Isothizaole Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Adhesives Or Adhesive Processes (AREA)

DD90342666A 1989-07-11 1990-07-10 Neue heterozyklische, stickstoff- und schwefelhaltige verbindungen, pharmazeutische zusammensetzungen, die dieselben enthalten und verfahren zu deren herstellung DD297973A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU893474A HU204040B (en)	1989-07-11	1989-07-11	Process for producing new thiazoles and thiazines and pharmaceutical compositions comprising same

Publications (1)

Publication Number	Publication Date
DD297973A5 true DD297973A5 (de)	1992-01-30

Family

ID=10964168

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90342666A DD297973A5 (de)	1989-07-11	1990-07-10	Neue heterozyklische, stickstoff- und schwefelhaltige verbindungen, pharmazeutische zusammensetzungen, die dieselben enthalten und verfahren zu deren herstellung

Country Status (24)

Country	Link
US (1)	US5096902A (ja)
EP (1)	EP0411775B1 (ja)
JP (1)	JPH0348670A (ja)
KR (1)	KR950003496B1 (ja)
CN (1)	CN1028229C (ja)
AT (1)	ATE135349T1 (ja)
AU (1)	AU629660B2 (ja)
CA (1)	CA2020805A1 (ja)
DD (1)	DD297973A5 (ja)
DE (1)	DE69025819T2 (ja)
FI (1)	FI903473A7 (ja)
HR (1)	HRP920775A2 (ja)
HU (2)	HU204040B (ja)
IE (1)	IE902499A1 (ja)
IL (1)	IL95018A (ja)
LT (1)	LTIP1775A (ja)
LV (1)	LV10090B (ja)
NO (1)	NO903078L (ja)
NZ (1)	NZ234440A (ja)
PL (2)	PL165110B1 (ja)
PT (1)	PT94653A (ja)
RU (1)	RU1833377C (ja)
YU (1)	YU47797B (ja)
ZA (1)	ZA905406B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2088965T3 (es) *	1989-04-07	1996-10-01	Lilly Co Eli	Derivados de rodanina aril-sustituidos.
US5458793A (en) *	1993-05-13	1995-10-17	The Lubrizol Corporation	Compositions useful as additives for lubricants and liquid fuels

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU78421A1 (fr) *	1977-10-31	1979-06-01	Zyma Sa	Procede de preparation de nouveaux composes thiazolidiniques
US4656286A (en) *	1984-08-27	1987-04-07	Polaroid Corporation, Patent Dept.	Aminoethanethiol and thiazolidine compounds
US4652649A (en) *	1985-02-20	1987-03-24	United Pharmaceuticals, Inc.	Anti-spasmodic agents having a ring in the main chain
HU198012B (en) *	1987-07-03	1989-07-28	Richter Gedeon Vegyeszet	Process for producing cyclic amino-acid derivatives and pharmaceutical compositions containing them
CA2004028C (en) *	1988-12-08	1998-09-22	Motoki Torizuka	Condensed benzene derivative

1989
- 1989-07-11 HU HU893474A patent/HU204040B/hu not_active IP Right Cessation
1990
- 1990-04-12 US US07/509,473 patent/US5096902A/en not_active Expired - Fee Related
- 1990-07-10 PL PL90300985A patent/PL165110B1/pl unknown
- 1990-07-10 CN CN90104518A patent/CN1028229C/zh not_active Expired - Fee Related
- 1990-07-10 EP EP90307527A patent/EP0411775B1/en not_active Expired - Lifetime
- 1990-07-10 FI FI903473A patent/FI903473A7/fi not_active Application Discontinuation
- 1990-07-10 ZA ZA905406A patent/ZA905406B/xx unknown
- 1990-07-10 RU SU904830514A patent/RU1833377C/ru active
- 1990-07-10 IL IL9501890A patent/IL95018A/en not_active IP Right Cessation
- 1990-07-10 IE IE249990A patent/IE902499A1/en not_active Application Discontinuation
- 1990-07-10 KR KR90010436A patent/KR950003496B1/ko not_active Expired - Lifetime
- 1990-07-10 AU AU58815/90A patent/AU629660B2/en not_active Ceased
- 1990-07-10 DE DE69025819T patent/DE69025819T2/de not_active Expired - Fee Related
- 1990-07-10 NZ NZ234440A patent/NZ234440A/xx unknown
- 1990-07-10 CA CA002020805A patent/CA2020805A1/en not_active Abandoned
- 1990-07-10 PL PL90285992A patent/PL165125B1/pl unknown
- 1990-07-10 DD DD90342666A patent/DD297973A5/de not_active IP Right Cessation
- 1990-07-10 YU YU133390A patent/YU47797B/sh unknown
- 1990-07-10 NO NO90903078A patent/NO903078L/no unknown
- 1990-07-10 PT PT94653A patent/PT94653A/pt not_active Application Discontinuation
- 1990-07-10 AT AT90307527T patent/ATE135349T1/de not_active IP Right Cessation
- 1990-07-11 JP JP2181698A patent/JPH0348670A/ja active Pending
1992
- 1992-10-01 HR HRP920775AA patent/HRP920775A2/hr not_active Application Discontinuation
- 1992-12-30 LV LVP-92-685A patent/LV10090B/lv unknown
1994
- 1994-01-14 LT LTIP1775A patent/LTIP1775A/xx not_active Application Discontinuation
- 1994-10-12 HU HU94P/P00038P patent/HU210074A9/hu unknown

Also Published As

Publication number	Publication date
US5096902A (en)	1992-03-17
ZA905406B (en)	1991-04-24
RU1833377C (en)	1993-08-07
JPH0348670A (ja)	1991-03-01
HRP920775A2 (hr)	1994-04-30
CN1028229C (zh)	1995-04-19
CA2020805A1 (en)	1991-01-12
KR950003496B1 (en)	1995-04-13
NO903078D0 (no)	1990-07-10
YU133390A (sh)	1992-09-07
PL285992A1 (en)	1991-02-25
LTIP1775A (en)	1995-07-25
ATE135349T1 (de)	1996-03-15
FI903473A0 (fi)	1990-07-10
YU47797B (sr)	1996-01-09
FI903473A7 (fi)	1991-01-12
PL165125B1 (pl)	1994-11-30
EP0411775B1 (en)	1996-03-13
EP0411775A1 (en)	1991-02-06
HUT55768A (en)	1991-06-28
NO903078L (no)	1991-01-14
DE69025819T2 (de)	1996-09-05
HU210074A9 (en)	1995-02-28
IL95018A (en)	1995-05-26
CN1049159A (zh)	1991-02-13
AU5881590A (en)	1991-01-17
IE902499A1 (en)	1991-02-13
LV10090B (en)	1995-02-20
HU204040B (en)	1991-11-28
PT94653A (pt)	1991-04-18
DE69025819D1 (de)	1996-04-18
LV10090A (lv)	1994-05-10
AU629660B2 (en)	1992-10-08
IL95018A0 (en)	1991-06-10
PL165110B1 (pl)	1994-11-30
NZ234440A (en)	1991-09-25
KR910002819A (ko)	1991-02-26

Legal Events

Date	Code	Title	Description
1999-01-07	ENJ	Ceased due to non-payment of renewal fee

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DE68927254T2 (de)	1997-02-06	Arylpiperidin-Derivate
CH647767A5 (de)	1985-02-15	Triazolverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel.
DD209622A5 (de)	1984-05-16	Verfahren zur herstellung von 1,4-dihydropyridinen
CS229940B2 (en)	1984-07-16	Production method substiuted pyridazine derivatives
DD215544A5 (de)	1984-11-14	Verfahren zur herstellung von dihydropyridinen
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DE69902851T2 (de)	2003-05-28	Nitronderivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
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DE69519315T2 (de)	2001-05-31	Aminoalkyl Benzoxazolinone und Benzothiazolinone, Verfahren zu deren Herstellung und sie enthaltende Zusammensetzungen
CH647519A5 (de)	1985-01-31	Bluthochdruck senkende amine.
DE1795822C2 (de)	1982-07-15	Thiazolylalkancarbonsäuren, Verfahren zu ihrer Herstellung und antiphlogistische Zubereitung
DE19502699A1 (de)	1996-08-01	Arylalkyl-thiadiazinone
DE1917432C2 (de)	1983-10-06	4-Hydroxythiazoline, deren Herstellung und Verwendung
DD297973A5 (de)	1992-01-30	Neue heterozyklische, stickstoff- und schwefelhaltige verbindungen, pharmazeutische zusammensetzungen, die dieselben enthalten und verfahren zu deren herstellung
DE3324771A1 (de)	1984-01-12	Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH645368A5 (de)	1984-09-28	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung.
DE2717415A1 (de)	1977-11-10	Verfahren zur herstellung von phenylpiperazinderivaten, phenylpiperazinderivate und diese enthaltende pharmazeutische zubereitungen
DE3035688A1 (de)	1981-04-16	2-amino-3-benzoyl-phenylacetamid-derivate, pharmazeutische zubereitungen, welche diese verbindungen enthalten und verfahren zu ihrer herstellung
DE2425767A1 (de)	1975-01-09	3-alkyl-9-aminoalkyl-1,2,3,4-tetrahydrocarbazole und ihre verwendung in arzneimitteln
DD209194A5 (de)	1984-04-25	Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden pyrimidon-derivaten
DD253616A5 (de)	1988-01-27	Verfahren zur herstellung von neuen pleunromutilinderivaten
DE2943326C2 (ja)	1988-09-15
EP0110298B1 (de)	1988-06-01	Acridanon-Derivate