JPS6169777A - キサンチニルメチルチアゾリジン、その製法およびそれを含有する医薬組成物 - Google Patents

キサンチニルメチルチアゾリジン、その製法およびそれを含有する医薬組成物

Info

Publication number: JPS6169777A
Authority: JP; Japan
Prior art keywords: group; formula; methyl; dimethylxanthine; carbon atoms
Prior art date: 1984-07-27
Legal status (The legal status 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 status listed.): Granted

Application number

JP16661985A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0335320B2 (fr

Inventor

シルバーノ・スピネリ

ライモンド・ルツソ

オドアルド・トフアネツチ

セルジオ・トグネラ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Italia SpA

Original Assignee

Boehringer Biochemia Robin SpA

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.)

1984-07-27

Filing date

1985-07-26

Publication date

1986-04-10

1985-07-26 Application filed by Boehringer Biochemia Robin SpA filed Critical Boehringer Biochemia Robin SpA

1986-04-10 Publication of JPS6169777A publication Critical patent/JPS6169777A/ja

1991-05-27 Publication of JPH0335320B2 publication Critical patent/JPH0335320B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
239000000203 mixture Substances 0.000 title description 30
UHVDMZDTAFXHAH-UHFFFAOYSA-N 8-(1,3-thiazolidin-2-ylmethyl)-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)NC(=O)NC=2N=C1CC1NCCS1 UHVDMZDTAFXHAH-UHFFFAOYSA-N 0.000 title description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 172
-1 1,3-dimethylxanthine-7-yl Chemical group 0.000 claims description 98
150000001875 compounds Chemical class 0.000 claims description 78
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
125000004432 carbon atom Chemical group C* 0.000 claims description 54
239000000126 substance Substances 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 25
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000003277 amino group Chemical group 0.000 claims description 11
230000000954 anitussive effect Effects 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
239000002585 base Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000001033 ether group Chemical group 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000001105 regulatory effect Effects 0.000 claims description 3
229940014800 succinic anhydride Drugs 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000000101 thioether group Chemical group 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000005012 alkyl thioether group Chemical group 0.000 claims description 2
150000001540 azides Chemical class 0.000 claims description 2
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 2
125000005208 trialkylammonium group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims 4
238000006957 Michael reaction Methods 0.000 claims 1
230000003182 bronchodilatating effect Effects 0.000 claims 1
230000000269 nucleophilic effect Effects 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
239000000243 solution Substances 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
206010011224 Cough Diseases 0.000 description 30
239000002904 solvent Substances 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
210000003097 mucus Anatomy 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000000725 suspension Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
238000000034 method Methods 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
206010036790 Productive cough Diseases 0.000 description 7
229940124584 antitussives Drugs 0.000 description 7
238000010992 reflux Methods 0.000 description 7
208000024794 sputum Diseases 0.000 description 7
210000003802 sputum Anatomy 0.000 description 7
238000011282 treatment Methods 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000009471 action Effects 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
206010006451 bronchitis Diseases 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
238000012360 testing method Methods 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
230000001575 pathological effect Effects 0.000 description 5
230000004044 response Effects 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
241000700198 Cavia Species 0.000 description 4
241000700199 Cavia porcellus Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 4
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000012545 processing Methods 0.000 description 4
SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 4
YNCPXBIZAPNQIJ-UHFFFAOYSA-N 1h-imidazole;sodium Chemical compound [Na].C1=CNC=N1 YNCPXBIZAPNQIJ-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 3
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 3
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 3
SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 3
239000003434 antitussive agent Substances 0.000 description 3
210000000621 bronchi Anatomy 0.000 description 3
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239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229960003067 cystine Drugs 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
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239000003607 modifier Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
150000003904 phospholipids Chemical class 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
241000894007 species Species 0.000 description 3
150000003548 thiazolidines Chemical class 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LXIWYKGAOIXZFO-UHFFFAOYSA-N 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetaldehyde Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC=O)C=N2 LXIWYKGAOIXZFO-UHFFFAOYSA-N 0.000 description 2
NULDEVQACXJZLL-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethylazanium;chloride Chemical compound Cl.NCCSSCCN NULDEVQACXJZLL-UHFFFAOYSA-N 0.000 description 2
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
206010006458 Bronchitis chronic Diseases 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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230000009057 passive transport Effects 0.000 description 1
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238000011458 pharmacological treatment Methods 0.000 description 1
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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 description 1
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LKFCPWBGBPJDRC-UHFFFAOYSA-M potassium;thiobenzate Chemical compound [K+].[O-]C(=S)C1=CC=CC=C1 LKFCPWBGBPJDRC-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
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KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 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
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210000002460 smooth muscle Anatomy 0.000 description 1
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235000019345 sodium thiosulphate Nutrition 0.000 description 1
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239000007921 spray Substances 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
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206010042772 syncope Diseases 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
210000005090 tracheal smooth muscle Anatomy 0.000 description 1
QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
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238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP16661985A 1984-07-27 1985-07-26 キサンチニルメチルチアゾリジン、その製法およびそれを含有する医薬組成物 Granted JPS6169777A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IT22088A/84		1984-07-27
IT8422088A IT1213197B (it)	1984-07-27	1984-07-27	Xantinilmetil-tiazolidine e composizioni farmaceutiche che le contengono.
IT21323A/85		1985-06-27

Publications (2)

Publication Number	Publication Date
JPS6169777A true JPS6169777A (ja)	1986-04-10
JPH0335320B2 JPH0335320B2 (fr)	1991-05-27

Family

ID=11191324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16661985A Granted JPS6169777A (ja)	1984-07-27	1985-07-26	キサンチニルメチルチアゾリジン、その製法およびそれを含有する医薬組成物

Country Status (2)

Country	Link
JP (1)	JPS6169777A (fr)
IT (1)	IT1213197B (fr)

1984
- 1984-07-27 IT IT8422088A patent/IT1213197B/it active
1985
- 1985-07-26 JP JP16661985A patent/JPS6169777A/ja active Granted

Also Published As

Publication number	Publication date
IT8422088A0 (it)	1984-07-27
IT1213197B (it)	1989-12-14
JPH0335320B2 (fr)	1991-05-27

Publication	Publication Date	Title
EP1442030B1 (fr)	2006-08-30	Antineoplasiques a base de thiopenesulfonamides et de thiazolesulfonamides
JPH021141B2 (fr)	1990-01-10
KR890004127B1 (ko)	1989-10-21	항염 작용을 갖는 피롤아세트 아미드의 제조방법
JPS6344753B2 (fr)	1988-09-06
AU656146B2 (en)	1995-01-27	Thiazolidin derivatives
HU229427B1 (en)	2013-12-30	Quinoline derivatives, process for producing them and pharmaceutical compositions containing them
DE3033169A1 (de)	1981-03-19	3,4-disubstituierte 1,2,5-thiadiazol-1-oxide und -1,1-dioxide
JPH0236159A (ja)	1990-02-06	化学化合物類
JPH0239507B2 (fr)	1990-09-05
RU2330034C1 (ru)	2008-07-27	[4-(5-аминометил-2-фторфенил)-пеперидин-1-ил]-(4-бром-3-метил-5-пропокситиофен-2-ил)-метанон гидрохлорид как ингибитор триптазы тучных клеток
Paris et al.	1980	Glycerides as prodrugs. 3. Synthesis and antiinflammatory activity of [1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl] glycerides (indomethacin glycerides)
DK149025B (da)	1985-12-23	Analogifremgangsmaade til fremstilling af vandoploeselige salte af n-(2-pyridyl)-2-methyl-4-hydroxy-2h-1,2-benzothiazin-3-carboxamid-1,1-dioxid
WO1997003060A1 (fr)	1997-01-30	Derives de la piperazine et leurs utilisations
JPS6163669A (ja)	1986-04-01	２−置換チアゾリジン、その製法およびそれを含有する鎮咳および粘液調整剤
JPH1171351A (ja)	1999-03-16	置換キノロン誘導体及びこれを含有する医薬
JPS6216942B2 (fr)	1987-04-15
FI79524C (fi)	1990-01-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-fenyl-4-oxo-2-ensmoersyraderivat.
US4551453A (en)	1985-11-05	2-(ω-Alkylaminoalkyl)- and 2-(ω-dialkylaminoalkyl-3-(4-X-benzylidene)-phthalimidines
WO1993001163A1 (fr)	1993-01-21	Derive amino acide
EP0053017B1 (fr)	1985-02-20	Dérivés amidiques
JPS6326748B2 (fr)	1988-05-31
JPS6169777A (ja)	1986-04-10	キサンチニルメチルチアゾリジン、その製法およびそれを含有する医薬組成物
JPS6129342B2 (fr)	1986-07-05
EP0171005B1 (fr)	1989-11-23	Xanthinylméthylthiazolidines, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4405638A (en)	1983-09-20	2-Methoxyphenyl esters of N-substituted amino acids, a process for their preparation and pharmaceutical compositions containing them