SE451135B - Tiopyranopyrimidinforeningar och syraadditionssalter derav - Google Patents

Tiopyranopyrimidinforeningar och syraadditionssalter derav

Info

Publication number: SE451135B
Authority: SE; Sweden
Prior art keywords: pyrimidine; dihydro; thiopyrano; group; piperazino
Prior art date: 1982-02-25

Application number

SE8301038A

Other languages

English (en)

Swedish (sv)

Other versions

SE8301038D0 (sv

SE8301038L (sv

Inventor

S Ohno

K Mizukoshi

O Komatsu

H Yamamoto

Y Kunou

Original Assignee

Maruko Pharmaceutical Co

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.)

1982-02-25

Filing date

1983-02-24

Publication date

1987-09-07

1982-02-25 Priority claimed from JP57029594A external-priority patent/JPS58146586A/ja

1983-02-01 Priority claimed from JP58015097A external-priority patent/JPS59141583A/ja

1983-02-24 Application filed by Maruko Pharmaceutical Co filed Critical Maruko Pharmaceutical Co

1983-02-24 Publication of SE8301038D0 publication Critical patent/SE8301038D0/xx

1983-08-26 Publication of SE8301038L publication Critical patent/SE8301038L/xx

1987-09-07 Publication of SE451135B publication Critical patent/SE451135B/sv

Links

150000001875 compounds Chemical class 0.000 title claims description 67
239000002253 acid Substances 0.000 title claims description 19
150000003839 salts Chemical class 0.000 title claims description 17
-1 Thiopyranopyrimidine compound Chemical class 0.000 claims description 42
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
DOUCQUNTDJUTAG-UHFFFAOYSA-N 4-(2-piperazin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)morpholine Chemical group C1CCSC2=C1N=C(N1CCNCC1)N=C2N1CCOCC1 DOUCQUNTDJUTAG-UHFFFAOYSA-N 0.000 claims description 3
GKEKTQPBVLFOMV-UHFFFAOYSA-N 4-piperazin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-2-amine Chemical group N=1C(N)=NC=2CCCSC=2C=1N1CCNCC1 GKEKTQPBVLFOMV-UHFFFAOYSA-N 0.000 claims description 3
VPXHNCJNSBHLJK-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=NC(N)=C(SCCC2)C2=N1 VPXHNCJNSBHLJK-UHFFFAOYSA-N 0.000 claims description 2
KMPUACMJNGJZDJ-UHFFFAOYSA-N 2-piperazin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-amine Chemical group N=1C=2CCCSC=2C(N)=NC=1N1CCNCC1 KMPUACMJNGJZDJ-UHFFFAOYSA-N 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
CLNFWLHXPORYNL-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-pyrrolidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical group C1CN(C)CCN1C(N=C1N2CCCC2)=NC2=C1SCCC2 CLNFWLHXPORYNL-UHFFFAOYSA-N 0.000 claims 1
UAGJRRHKKNBEFG-UHFFFAOYSA-N 2-piperazin-1-yl-4-pyrrolidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical group C1CCCN1C1=NC(N2CCNCC2)=NC2=C1SCCC2 UAGJRRHKKNBEFG-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
238000002844 melting Methods 0.000 description 56
230000008018 melting Effects 0.000 description 56
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
239000000203 mixture Substances 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
239000013078 crystal Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 19
238000012360 testing method Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 18
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 14
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
241000699670 Mus sp. Species 0.000 description 13
238000000034 method Methods 0.000 description 13
210000004369 blood Anatomy 0.000 description 12
239000008280 blood Substances 0.000 description 12
239000007858 starting material Substances 0.000 description 12
239000003208 petroleum Substances 0.000 description 11
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
229940093956 potassium carbonate Drugs 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
238000003756 stirring Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 7
239000012458 free base Substances 0.000 description 7
229960004592 isopropanol Drugs 0.000 description 7
239000000047 product Substances 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 6
HIKOVOQFJFSCLL-UHFFFAOYSA-N 2,4-dichloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical compound S1CCCC2=NC(Cl)=NC(Cl)=C21 HIKOVOQFJFSCLL-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000011976 maleic acid Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000005303 weighing Methods 0.000 description 5
VEDQDDFGBYQFJP-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-piperazin-1-yl-4-pyrrolidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical compound OC(=O)\C=C/C(O)=O.C1CCCN1C1=NC(N2CCNCC2)=NC2=C1SCCC2 VEDQDDFGBYQFJP-BTJKTKAUSA-N 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
BBKLBCWAKGLQLA-UHFFFAOYSA-N 2-chloro-4-pyrrolidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical compound N=1C(Cl)=NC=2CCCSC=2C=1N1CCCC1 BBKLBCWAKGLQLA-UHFFFAOYSA-N 0.000 description 4
BYDDYIAAWSEFJA-UHFFFAOYSA-N 4-chloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-2-amine Chemical compound S1CCCC2=NC(N)=NC(Cl)=C21 BYDDYIAAWSEFJA-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000037396 body weight Effects 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000002218 hypoglycaemic effect Effects 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
210000003462 vein Anatomy 0.000 description 4
ZRSGSXGGDIEONU-SPIKMXEPSA-N (Z)-but-2-enedioic acid 4-piperazin-1-yl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-2-amine Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.N=1C(N)=NC=2CCCSC=2C=1N1CCNCC1 ZRSGSXGGDIEONU-SPIKMXEPSA-N 0.000 description 3
CSTUECNOOZVIPD-UHFFFAOYSA-N 4-(2-chloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)morpholine Chemical compound N=1C(Cl)=NC=2CCCSC=2C=1N1CCOCC1 CSTUECNOOZVIPD-UHFFFAOYSA-N 0.000 description 3
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 3
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229960005371 tolbutamide Drugs 0.000 description 3
WHYBPOZCWTUCOB-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(4-methylpiperazin-1-yl)-4-pyrrolidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1C(N=C1N2CCCC2)=NC2=C1SCCC2 WHYBPOZCWTUCOB-BTJKTKAUSA-N 0.000 description 2
FPGHRAKCQIEGEZ-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-(2-piperazin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)morpholine Chemical compound OC(=O)\C=C/C(O)=O.C1CCSC2=C1N=C(N1CCNCC1)N=C2N1CCOCC1 FPGHRAKCQIEGEZ-BTJKTKAUSA-N 0.000 description 2
MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
PJIIOCXBXURAMP-UHFFFAOYSA-N 2-[(2-chloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)amino]ethanol Chemical compound C1CCSC2=C1N=C(Cl)N=C2NCCO PJIIOCXBXURAMP-UHFFFAOYSA-N 0.000 description 2
OVSRTBOZBHONQW-UHFFFAOYSA-N 2-amino-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one Chemical compound S1CCCC2=NC(N)=NC(O)=C21 OVSRTBOZBHONQW-UHFFFAOYSA-N 0.000 description 2
YVIZUDQMKQIGCZ-UHFFFAOYSA-N 2-chloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-amine Chemical compound C1CCSC2=C1N=C(Cl)N=C2N YVIZUDQMKQIGCZ-UHFFFAOYSA-N 0.000 description 2
CQXAAPQFTXYFOR-UHFFFAOYSA-N 4-(2-chloro-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)piperazine-1-carbaldehyde Chemical compound N=1C(Cl)=NC=2CCCSC=2C=1N1CCN(C=O)CC1 CQXAAPQFTXYFOR-UHFFFAOYSA-N 0.000 description 2
LCLDBDPNEUHPCS-UHFFFAOYSA-N 4-(2-piperidin-1-yl-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl)piperazine-1-carbaldehyde Chemical compound C1CN(C=O)CCN1C1=NC(N2CCCCC2)=NC2=C1SCCC2 LCLDBDPNEUHPCS-UHFFFAOYSA-N 0.000 description 2
QZLCXQDMDHCCNK-UHFFFAOYSA-N 4-[2-(methylamino)-7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidin-4-yl]piperazine-1-carbaldehyde Chemical compound N=1C(NC)=NC=2CCCSC=2C=1N1CCN(C=O)CC1 QZLCXQDMDHCCNK-UHFFFAOYSA-N 0.000 description 2
JZVMJDFWTRHHPA-UHFFFAOYSA-N 7,8-dihydro-6h-thiopyrano[3,2-d]pyrimidine Chemical compound N1=CN=C2CCCSC2=C1 JZVMJDFWTRHHPA-UHFFFAOYSA-N 0.000 description 2
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230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000001387 anti-histamine Effects 0.000 description 2
239000000739 antihistaminic agent Substances 0.000 description 2
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SCPOPPZYKMBXRM-UHFFFAOYSA-N boric acid;2-methylaniline Chemical compound OB(O)O.CC1=CC=CC=C1N SCPOPPZYKMBXRM-UHFFFAOYSA-N 0.000 description 2
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125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
229960000520 diphenhydramine Drugs 0.000 description 2
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229910052717 sulfur Inorganic materials 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SE8301038A 1982-02-25 1983-02-24 Tiopyranopyrimidinforeningar och syraadditionssalter derav SE451135B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP57029594A JPS58146586A (ja)	1982-02-25	1982-02-25	チオピラノピリミジン誘導体およびその酸付加塩
JP58015097A JPS59141583A (ja)	1983-02-01	1983-02-01	チオピラノピリミジン誘導体およびその酸付加塩

Publications (3)

Publication Number	Publication Date
SE8301038D0 SE8301038D0 (sv)	1983-02-24
SE8301038L SE8301038L (sv)	1983-08-26
SE451135B true SE451135B (sv)	1987-09-07

Family

ID=26351189

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8301038A SE451135B (sv)	1982-02-25	1983-02-24	Tiopyranopyrimidinforeningar och syraadditionssalter derav

Country Status (12)

Country	Link
US (1)	US4435566A (de)
KR (1)	KR840003638A (de)
CA (1)	CA1217186A (de)
CH (1)	CH651305A5 (de)
DE (1)	DE3306485A1 (de)
ES (2)	ES8504810A1 (de)
FR (1)	FR2522000B1 (de)
GB (1)	GB2119368B (de)
HU (1)	HU189666B (de)
IT (1)	IT1212855B (de)
NL (1)	NL8300656A (de)
SE (1)	SE451135B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0224722B1 (de) *	1985-11-04	1993-01-07	Merck & Co. Inc.	Verwendung von 6H-7,8-Dihydrothiapyrano[3,2d]pyrimidinen zur Herstellung von Arzneimitteln zur Verwendung als hypoglykämische Mittel oder als Abmagerungsmittel für fettsüchtige Patienten
US4978667A (en) *	1986-12-15	1990-12-18	Merck & Co., Inc.	Substituted 6H-7,8-dihydrothiapyrano(3,2-d)-pyrimidines as hypoglycemic agents
US4889856A (en) *	1987-08-31	1989-12-26	Merck & Co., Inc.	7,8-dihydro-4-(1-pierazinyl)-6H-thiopyrano-[3,2-d] pyrimidines as β-blockers
US4871739A (en) *	1987-01-21	1989-10-03	Merck & Co., Inc.	Substituted 6H-7,8-dihydrothiapyrano(3,2-D)-pyrimidines as hyopglycemic agents
US5057517A (en) *	1987-07-20	1991-10-15	Merck & Co., Inc.	Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents
US4994464A (en) *	1987-08-31	1991-02-19	Merck & Co., Inc.	Piperazinylpyrimidines as β-adrenergic receptor blockers
EP0335979A4 (en) *	1987-09-16	1992-02-26	Taiho Pharmaceutical Company, Limited	Thienopyrimidine derivatives
US5869486A (en) *	1995-02-24	1999-02-09	Ono Pharmaceutical Co., Ltd.	Fused pyrimidines and pyriazines as pharmaceutical compounds
PT757984E (pt) *	1995-08-08	2003-02-28	Ono Pharmaceutical Co	Derivados de acido hidroxamico uteis para inibir a gelatinase

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB951432A (en) *	1959-03-17	1964-03-04	Wellcome Found	Pyrimidine derivatives and the manufacture thereof
DE1470336A1 (de)	1962-07-04	1969-03-20	Thomae Gmbh Dr K	Neue Dihydrothieno-[3,4-d]-pyrimidine und Verfahren zu ihrer Herstellung
DE1251765B (de) *	1963-07-23	1967-10-12	Dr Karl Thomae Gesellschaft mit beschrankter Haftung Biberach/Riß	Verfahren zur Herstellung von neuen 5H - Dihydrothiopyrano [4 3 d] pynmidinen

1983
- 1983-02-22 NL NL8300656A patent/NL8300656A/nl not_active Application Discontinuation
- 1983-02-23 IT IT8347764A patent/IT1212855B/it active
- 1983-02-24 GB GB08305175A patent/GB2119368B/en not_active Expired
- 1983-02-24 DE DE19833306485 patent/DE3306485A1/de not_active Ceased
- 1983-02-24 CA CA000422274A patent/CA1217186A/en not_active Expired
- 1983-02-24 KR KR1019830000757A patent/KR840003638A/ko not_active Withdrawn
- 1983-02-24 ES ES520075A patent/ES8504810A1/es not_active Expired
- 1983-02-24 HU HU83641A patent/HU189666B/hu not_active IP Right Cessation
- 1983-02-24 SE SE8301038A patent/SE451135B/sv not_active IP Right Cessation
- 1983-02-25 CH CH1077/83A patent/CH651305A5/de not_active IP Right Cessation
- 1983-02-25 FR FR8303183A patent/FR2522000B1/fr not_active Expired
- 1983-02-25 US US06/469,657 patent/US4435566A/en not_active Expired - Fee Related
1984
- 1984-11-30 ES ES538649A patent/ES8604597A1/es not_active Expired

Also Published As

Publication number	Publication date
ES520075A0 (es)	1985-05-16
FR2522000B1 (fr)	1986-11-07
KR840003638A (ko)	1984-09-15
CA1217186A (en)	1987-01-27
ES8504810A1 (es)	1985-05-16
GB2119368A (en)	1983-11-16
IT8347764A0 (it)	1983-02-23
NL8300656A (nl)	1983-09-16
HU189666B (en)	1986-07-28
GB2119368B (en)	1985-10-16
SE8301038D0 (sv)	1983-02-24
ES538649A0 (es)	1986-02-16
IT1212855B (it)	1989-11-30
DE3306485A1 (de)	1983-09-08
ES8604597A1 (es)	1986-02-16
US4435566A (en)	1984-03-06
GB8305175D0 (en)	1983-03-30
SE8301038L (sv)	1983-08-26
CH651305A5 (de)	1985-09-13
FR2522000A1 (fr)	1983-08-26

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