CZ70594A3 - Thiadiazinones - Google Patents

Thiadiazinones Download PDF

Info

Publication number: CZ70594A3
Authority: CZ; Czechia
Prior art keywords: dihydro; ethyl; thiadiazin; formula; compound
Prior art date: 1993-04-01

Application number

CZ94705A

Other languages

Czech (cs)

English (en)

Inventor

Rochus Jonas

Michael Klockow

Hans-Jochen Schliep

Michael Wolf

Original Assignee

Merck Patent Gmbh

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.)

1993-04-01

Filing date

1994-03-25

Publication date

1994-12-15

1994-03-25 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1994-12-15 Publication of CZ70594A3 publication Critical patent/CZ70594A3/cs

Links

-1 methylenedioxy Chemical group 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
KFJJKQPQLLMDIQ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[3-(dimethylamino)propyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(CCCN(C)C)C(=O)SC1 KFJJKQPQLLMDIQ-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
BMGFMYTZEXBTEJ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-6-ethyl-6H-1,3,4-thiadiazin-2-one Chemical compound COC=1C=C(C=CC=1OC)N1C(SC(C=N1)CC)=O BMGFMYTZEXBTEJ-UHFFFAOYSA-N 0.000 claims 1
HIZIMUCPUGDGLO-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-(dimethylamino)-6,6-diethyl-1,3,4-thiadiazin-2-one Chemical compound CCC1(CC)SC(=O)N(N(C)C)N=C1C1=CC=C(OC)C(OC)=C1 HIZIMUCPUGDGLO-UHFFFAOYSA-N 0.000 claims 1
MTVLYWXDQXLLQF-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(3-morpholin-4-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CCCN1CCOCC1 MTVLYWXDQXLLQF-UHFFFAOYSA-N 0.000 claims 1
YSODXONESAHCBL-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(3-piperidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CCCN1CCCCC1 YSODXONESAHCBL-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
208000006673 asthma Diseases 0.000 abstract description 3
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 2
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 2
125000002947 alkylene group Chemical group 0.000 abstract description 2
125000003277 amino group Chemical group 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
230000002526 effect on cardiovascular system Effects 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000000126 substance Substances 0.000 description 8
HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 7
MLGXDYNVEUDWHZ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OC)=C1 MLGXDYNVEUDWHZ-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 6
KQUGNOYYBNPZBP-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)F)C(OC)=C1 KQUGNOYYBNPZBP-UHFFFAOYSA-N 0.000 description 6
SQXAROYMYJEJTP-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OCF)C(OC)=C1 SQXAROYMYJEJTP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
WTGUUGJZRZUIAU-UHFFFAOYSA-N 1,3,4-thiadiazin-2-one Chemical compound O=C1N=NC=CS1 WTGUUGJZRZUIAU-UHFFFAOYSA-N 0.000 description 5
WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 5
LPVPITJSBXSDHT-UHFFFAOYSA-N 3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound O=C1NN=CCS1 LPVPITJSBXSDHT-UHFFFAOYSA-N 0.000 description 5
LVKFSJWCSIBHMY-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=NNC(=O)SC1CC LVKFSJWCSIBHMY-UHFFFAOYSA-N 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000003826 tablet Substances 0.000 description 5
RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 4
LELNKYUZHIIYJL-UHFFFAOYSA-N 5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)NN=2)CC)=C1 LELNKYUZHIIYJL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
WIVMBQZZIYHVCZ-UHFFFAOYSA-N 6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1 WIVMBQZZIYHVCZ-UHFFFAOYSA-N 0.000 description 3
CRVAECICDQAMRA-UHFFFAOYSA-N 6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)(F)F)C(OC)=C1 CRVAECICDQAMRA-UHFFFAOYSA-N 0.000 description 3
QYRSKTNORZKLKH-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3-(3-pyrrolidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CCCN1CCCC1 QYRSKTNORZKLKH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000013543 active substance Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 description 2
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
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241000282472 Canis lupus familiaris Species 0.000 description 2
241000700198 Cavia Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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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 2
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125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
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238000006266 etherification reaction Methods 0.000 description 2
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235000019322 gelatine Nutrition 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
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235000019271 petrolatum Nutrition 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
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239000000829 suppository Substances 0.000 description 2
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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UWMSQWJUWUFTFQ-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)N(CCN(C)C)N=2)CC)=C1 UWMSQWJUWUFTFQ-UHFFFAOYSA-N 0.000 description 1
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AXCBBCDRIZPVBW-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OCF)C(OC)=C1 AXCBBCDRIZPVBW-UHFFFAOYSA-N 0.000 description 1
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BIJUKXDAJSUOME-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-[3-methoxy-4-(1,1,2-trifluoroethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC(F)(F)CF)C(OC)=CC(C=2CSC(=O)N(CCCN(C)C)N=2)=C1 BIJUKXDAJSUOME-UHFFFAOYSA-N 0.000 description 1
VUQLCNWGPUYVGN-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC(F)(F)F)C(OC)=CC(C=2CSC(=O)N(CCCN(C)C)N=2)=C1 VUQLCNWGPUYVGN-UHFFFAOYSA-N 0.000 description 1
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125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
LNWHCOPMPXKPNZ-UHFFFAOYSA-N o-methyl n-aminocarbamothioate Chemical compound COC(=S)NN LNWHCOPMPXKPNZ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 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
239000011734 sodium Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CZ94705A 1993-04-01 1994-03-25 Thiadiazinones CZ70594A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4310699A DE4310699A1 (de)	1993-04-01	1993-04-01	Thiadiazinone

Publications (1)

Publication Number	Publication Date
CZ70594A3 true CZ70594A3 (en)	1994-12-15

Family

ID=6484473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ94705A CZ70594A3 (en)	1993-04-01	1994-03-25	Thiadiazinones

Country Status (12)

Country	Link
US (1)	US5434149A (2)
EP (1)	EP0618201A1 (2)
JP (1)	JPH072812A (2)
CN (1)	CN1101644A (2)
AU (1)	AU675488B2 (2)
CA (1)	CA2120301A1 (2)
CZ (1)	CZ70594A3 (2)
DE (1)	DE4310699A1 (2)
HU (1)	HUT70543A (2)
NO (1)	NO941150L (2)
SK (1)	SK38594A3 (2)
TW (1)	TW310326B (2)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19500558A1 (de) *	1995-01-11	1996-07-18	Merck Patent Gmbh	3-Alkoxycarbonyl-thiadiazinone
DE19502699A1 (de) *	1995-01-28	1996-08-01	Merck Patent Gmbh	Arylalkyl-thiadiazinone
DE19533975A1 (de) *	1995-09-14	1997-03-20	Merck Patent Gmbh	Arylalkyl-diazinone
ATE526020T1 (de) *	2000-08-10	2011-10-15	Cold Spring Harbor Lab	Gesteigertes kognitives training
US8153646B2 (en) *	2000-08-10	2012-04-10	Dart Neuroscience (Cayman) Ltd.	Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
US20050070529A1 (en) *	2001-02-12	2005-03-31	Merk Pantent Gmbh	Use of type 4 phosphodiesterase inhibitors in myocardial diseases
DE10150517A1 (de) *	2001-10-12	2003-04-17	Merck Patent Gmbh	Verwendung von Phosphodiesterase IV-Inhibitoren
EP1463509A1 (en) *	2001-10-31	2004-10-06	MERCK PATENT GmbH	Type 4 phosphodiesterase inhibitors and uses thereof
WO2005075437A1 (en) *	2004-02-04	2005-08-18	Altana Pharma Ag	Pyridazinone derivatives and their use as pde4 inhibitors
EP1716133B1 (en)	2004-02-04	2008-03-26	Nycomed GmbH	2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors
DE102007041115A1 (de)	2007-08-30	2009-03-05	Merck Patent Gmbh	Thiadiazinonderivate

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4413713Y1 (2) *	1967-04-26	1969-06-09
JPS54135785A (en) *	1978-04-12	1979-10-22	Yoshitomi Pharmaceut Ind Ltd	Pyridazinone derivative and its preparation
US4495185A (en) *	1981-11-12	1985-01-22	Imperial Chemical Industries, Plc	1,2,4-Triazin-3(2H) ones
US4489074A (en) *	1982-11-12	1984-12-18	Imperial Chemical Industries, Plc	1,3,4-Thiadiazin-2-ones
ES2131506T3 (es) *	1990-09-21	1999-08-01	Rohm & Haas	Dihidropiridacinonas y piridacinonas como fungicidas.

1993
- 1993-04-01 DE DE4310699A patent/DE4310699A1/de not_active Withdrawn
1994
- 1994-03-19 EP EP94104349A patent/EP0618201A1/de not_active Withdrawn
- 1994-03-23 AU AU57983/94A patent/AU675488B2/en not_active Expired - Fee Related
- 1994-03-25 CZ CZ94705A patent/CZ70594A3/cs unknown
- 1994-03-28 JP JP6057099A patent/JPH072812A/ja active Pending
- 1994-03-29 NO NO941150A patent/NO941150L/no unknown
- 1994-03-30 CA CA002120301A patent/CA2120301A1/en not_active Abandoned
- 1994-03-30 TW TW083102744A patent/TW310326B/zh active
- 1994-03-30 CN CN94104074A patent/CN1101644A/zh active Pending
- 1994-03-31 US US08/220,657 patent/US5434149A/en not_active Expired - Fee Related
- 1994-03-31 HU HU9400934A patent/HUT70543A/hu unknown
- 1994-03-31 SK SK385-94A patent/SK38594A3/sk unknown

Also Published As

Publication number	Publication date
CA2120301A1 (en)	1994-10-02
NO941150L (no)	1994-10-03
HUT70543A (en)	1995-10-30
NO941150D0 (no)	1994-03-29
CN1101644A (zh)	1995-04-19
SK38594A3 (en)	1994-12-07
DE4310699A1 (de)	1994-10-06
EP0618201A1 (de)	1994-10-05
AU675488B2 (en)	1997-02-06
AU5798394A (en)	1994-10-06
US5434149A (en)	1995-07-18
HU9400934D0 (en)	1994-06-28
JPH072812A (ja)	1995-01-06
TW310326B (2)	1997-07-11

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EP4188383A1 (en)	2023-06-07	Sos1 inhibitors
EP1277738A1 (en)	2003-01-22	Condensed heteroaryl derivatives
IL126591A (en)	2001-11-25	Saline dihydrate salts of -5 (-2 (-4 (1 (2, 2-benzothiazole - 3yl) -1-piperazinyl) ethyl) - 6-chloro-1, -3-dihydro-2 (1H) - indole - 2one (= ziprasidone) And pharmaceutical preparations containing them
WO2008038175A2 (en)	2008-04-03	Dithiolopyrrolones compounds and their therapeutic applications
CZ70594A3 (en)	1994-12-15	Thiadiazinones
WO2002016369A2 (en)	2002-02-28	Novel macrocycles and uses thereof
WO2004026226A2 (en)	2004-04-01	Compounds, compositions and methods
KR100384726B1 (ko)	2003-08-25	아릴알킬-티아디아지논유도체
KR20150060610A (ko)	2015-06-03	다이하이드로피리미딘 유도체의 결정질 형태
RU2345991C2 (ru)	2009-02-10	Хинолиновые производные
MX2008007687A (es)	2008-09-26	Compuestos y métodos para inhibir la interacción de proteínas bcl con compañeros enlazantes.
CZ321095A3 (en)	1996-09-11	Heterocyclic compounds
JPH04330078A (ja)	1992-11-18	抗緑内障剤としての置換チエノ［２，３−ｂ］［１，４］チアジン−６−スルホンアミド類
CA1207774A (en)	1986-07-15	1-phenylindazol-3-one compounds, a method of preparing them and pharmaceutical compositions containing these compounds
CZ263692A3 (en)	1993-05-12	Thiadiazinones, process of their preparation and pharmaceutical compositions based thereon
IE903975A1 (en)	1991-05-08	4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them
US3729477A (en)	1973-04-24	Certain 4-(3-amino-2-hydroxypropoxy)-1,2,5-thiadiazole-3-carboxamides
WO2022166923A1 (zh)	2022-08-11	苯基二氢嘧啶类化合物及其应用
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SK399A3 (en)	1999-06-11	Benzo[g]quinoline derivatives, process for their preparation, pharmaceutical composition containing same and their use
JP3068175B2 (ja)	2000-07-24	イソチアゾロ〔５，４―ｂ〕ピリジン誘導体