SE434836B - Tiazolidinforeningar - Google Patents

Tiazolidinforeningar

Info

Publication number: SE434836B
Authority: SE; Sweden
Prior art keywords: methylpropionyl; compound according; mercapto; acid; thiazolidinecarboxylic acid
Prior art date: 1977-06-29

Application number

SE7807335A

Other languages

English (en)

Swedish (sv)

Other versions

SE7807335L (sv

Inventor

K Arimura

S Murakami

T Oka

Original Assignee

Santen Pharmaceutical Co Ltd

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.)

1977-06-29

Filing date

1978-06-28

Publication date

1984-08-20

1977-06-29 Priority claimed from JP52078179A external-priority patent/JPS5834474B2/ja

1977-08-15 Priority claimed from JP9802477A external-priority patent/JPS6047264B2/ja

1978-06-28 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1978-12-30 Publication of SE7807335L publication Critical patent/SE7807335L/xx

1984-08-20 Publication of SE434836B publication Critical patent/SE434836B/sv

Links

OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 38
-1 Thiazolidine compound Chemical class 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
ULSZVNJBVJWEJE-GSVOUGTGSA-N (2r)-1,3-thiazolidin-3-ium-2-carboxylate Chemical compound [O-]C(=O)[C@@H]1[NH2+]CCS1 ULSZVNJBVJWEJE-GSVOUGTGSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
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 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229940030600 antihypertensive agent Drugs 0.000 claims description 3
239000002220 antihypertensive agent Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000003548 thiazolidines Chemical class 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
HNLLOXPIKATAAX-IQYSWEBNSA-N C(C)OC1=CC=C(C=C1)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O Chemical group C(C)OC1=CC=C(C=C1)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O HNLLOXPIKATAAX-IQYSWEBNSA-N 0.000 claims description 2
CNECAFLAFVOZMC-JRIBOLAGSA-N ClC1=C(C(=CC=C1)Cl)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O Chemical group ClC1=C(C(=CC=C1)Cl)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O CNECAFLAFVOZMC-JRIBOLAGSA-N 0.000 claims description 2
RWZDBICNMCHKKP-PEUVISTOSA-N SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)OC)C Chemical group SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)OC)C RWZDBICNMCHKKP-PEUVISTOSA-N 0.000 claims description 2
NIWNDAOLYHKBFL-AXDSSHIGSA-N SCC(C(=O)N1[C@@H](CSC11CCCCC1)C(=O)O)C Chemical group SCC(C(=O)N1[C@@H](CSC11CCCCC1)C(=O)O)C NIWNDAOLYHKBFL-AXDSSHIGSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
125000003545 alkoxy group Chemical group 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
125000001589 carboacyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
150000002431 hydrogen Chemical group 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
CVBOMOZXEDQERR-MEXZMNCTSA-N (4R)-3-(3-acetylsulfanyl-2-methylpropanoyl)-2-(3-nitrophenyl)-1,3-thiazolidine-4-carboxylic acid Chemical group C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C CVBOMOZXEDQERR-MEXZMNCTSA-N 0.000 claims 1
URLRVICMGRSFRR-MEXZMNCTSA-N (4R)-3-(3-acetylsulfanyl-2-methylpropanoyl)-2-(4-fluorophenyl)-1,3-thiazolidine-4-carboxylic acid Chemical group C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)F)C URLRVICMGRSFRR-MEXZMNCTSA-N 0.000 claims 1
HUZUUTLWSUNZGF-BHKPVTDMSA-N C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)OC)C Chemical group C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)OC)C HUZUUTLWSUNZGF-BHKPVTDMSA-N 0.000 claims 1
BEECIOWPCYAOKN-SAVVLTDYSA-N CC(CS)C(N1C(C(C=C2)=CC=C2Br)SC[C@H]1C(O)=O)=O Chemical group CC(CS)C(N1C(C(C=C2)=CC=C2Br)SC[C@H]1C(O)=O)=O BEECIOWPCYAOKN-SAVVLTDYSA-N 0.000 claims 1
DUVGBQUPPONYGY-MEXZMNCTSA-N CC(CSC(C)=O)C(N1C(C(C=C2)=CC=C2Br)SC[C@H]1C(O)=O)=O Chemical group CC(CSC(C)=O)C(N1C(C(C=C2)=CC=C2Br)SC[C@H]1C(O)=O)=O DUVGBQUPPONYGY-MEXZMNCTSA-N 0.000 claims 1
QURDQNGZVWEDBK-UQACVICXSA-N COC=1C=C(C=CC1OC)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O Chemical group COC=1C=C(C=CC1OC)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O QURDQNGZVWEDBK-UQACVICXSA-N 0.000 claims 1
APFXLUUSVFEUIV-ZQDGQSPWSA-N SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=C(C=CC=C1)OC)C Chemical group SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=C(C=CC=C1)OC)C APFXLUUSVFEUIV-ZQDGQSPWSA-N 0.000 claims 1
ASRXWUZFFLMQAJ-SAVVLTDYSA-N SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C Chemical group SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C ASRXWUZFFLMQAJ-SAVVLTDYSA-N 0.000 claims 1
BYHQPGLVHQUGQT-QDYJBQRPSA-N SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=CC=C1)C Chemical group SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=CC=C1)C BYHQPGLVHQUGQT-QDYJBQRPSA-N 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
206010020772 Hypertension Diseases 0.000 description 5
241000700159 Rattus Species 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
239000012442 inert solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
201000005857 malignant hypertension Diseases 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
OVSRBUIUCONCCD-KFJBMODSSA-N (3R)-4-(3-acetylsulfanyl-2-methylpropanoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid Chemical compound C(C)(=O)SCC(C(=O)N1[C@@H](CSC11CCCCC1)C(=O)O)C OVSRBUIUCONCCD-KFJBMODSSA-N 0.000 description 1
DQAJYPXRHVIJEC-PEUVISTOSA-N (4R)-2-(4-methoxyphenyl)-3-(2-methyl-3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)OC)C DQAJYPXRHVIJEC-PEUVISTOSA-N 0.000 description 1
CVBOMOZXEDQERR-XYWLETCASA-N (4R)-3-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]-2-(3-nitrophenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C(C)(=O)SC[C@H](C(=O)N1C(SC[C@H]1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C CVBOMOZXEDQERR-XYWLETCASA-N 0.000 description 1
FJMBKXDYYWGXHM-KNVGNIICSA-N (4R)-3-[4-(ethylamino)-4-oxobutanethioyl]-2-(4-methylphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C(C)NC(=O)CCC(=S)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)C FJMBKXDYYWGXHM-KNVGNIICSA-N 0.000 description 1
LESQASCTNMKKPZ-IENPIDJESA-N (4r)-2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@H](C(=O)O)CSC1C1=CC=C(Cl)C=C1 LESQASCTNMKKPZ-IENPIDJESA-N 0.000 description 1
ZQRSXNJVEHLFCE-RGURZIINSA-N (4r)-2-(4-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1SC[C@@H](C(O)=O)N1 ZQRSXNJVEHLFCE-RGURZIINSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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 1
VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
BEECIOWPCYAOKN-HCTSQKMQSA-N BrC1=CC=C(C=C1)C1SC[C@H](N1C([C@@H](CS)C)=O)C(=O)O Chemical compound BrC1=CC=C(C=C1)C1SC[C@H](N1C([C@@H](CS)C)=O)C(=O)O BEECIOWPCYAOKN-HCTSQKMQSA-N 0.000 description 1
101800004538 Bradykinin Proteins 0.000 description 1
102400000967 Bradykinin Human genes 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
AMVIAPWSDPSLTO-MEXZMNCTSA-N C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)Cl)C Chemical compound C(C)(=O)SCC(C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)Cl)C AMVIAPWSDPSLTO-MEXZMNCTSA-N 0.000 description 1
HUZUUTLWSUNZGF-NMGSQIIKSA-N C(C)(=O)SC[C@H](C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)OC)C Chemical compound C(C)(=O)SC[C@H](C(=O)N1C(SC[C@H]1C(=O)O)C1=CC=C(C=C1)OC)C HUZUUTLWSUNZGF-NMGSQIIKSA-N 0.000 description 1
VKCOGRQFLMEVLR-UHFFFAOYSA-N CCNCC.C1C=CNC1 Chemical compound CCNCC.C1C=CNC1 VKCOGRQFLMEVLR-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
PUXWRALAEGQBPQ-SAVVLTDYSA-N ClC1=CC=C(C=C1)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O Chemical compound ClC1=CC=C(C=C1)C1SC[C@H](N1C(C(CS)C)=O)C(=O)O PUXWRALAEGQBPQ-SAVVLTDYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
COXRPBBNPBCNDM-UHFFFAOYSA-N Dioxamide Natural products C1=C2OCOC2=CC(C=CC(=O)N(CCC=2C=C3OCOC3=CC=2)C)=C1 COXRPBBNPBCNDM-UHFFFAOYSA-N 0.000 description 1
QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
DZLNHFMRPBPULJ-VKHMYHEASA-N L-thioproline Chemical compound OC(=O)[C@@H]1CSCN1 DZLNHFMRPBPULJ-VKHMYHEASA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
METKWVOCJQCWHY-UHFFFAOYSA-N [O-]C([S+]1CNCC1)=O Chemical compound [O-]C([S+]1CNCC1)=O METKWVOCJQCWHY-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940124572 antihypotensive agent Drugs 0.000 description 1
150000001483 arginine derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical class O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000009989 contractile response Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000005856 malignant essential hypertension Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical class CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
230000036454 renin-angiotensin system Effects 0.000 description 1
LUDPWTHDXSOXDX-SCSAIBSYSA-N s-[(2r)-3-chloro-2-methyl-3-oxopropyl] ethanethioate Chemical compound ClC(=O)[C@H](C)CSC(C)=O LUDPWTHDXSOXDX-SCSAIBSYSA-N 0.000 description 1
LUDPWTHDXSOXDX-BYPYZUCNSA-N s-[(2s)-3-chloro-2-methyl-3-oxopropyl] ethanethioate Chemical compound ClC(=O)[C@@H](C)CSC(C)=O LUDPWTHDXSOXDX-BYPYZUCNSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SE7807335A 1977-06-29 1978-06-28 Tiazolidinforeningar SE434836B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP52078179A JPS5834474B2 (ja)	1977-06-29	1977-06-29	チアゾリジン誘導体の製造法
JP9802477A JPS6047264B2 (ja)	1977-08-15	1977-08-15	チアゾリジン誘導体

Publications (2)

Publication Number	Publication Date
SE7807335L SE7807335L (sv)	1978-12-30
SE434836B true SE434836B (sv)	1984-08-20

Family

ID=26419266

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7807335A SE434836B (sv)	1977-06-29	1978-06-28	Tiazolidinforeningar

Country Status (7)

Country	Link
DE (1)	DE2828578C2 (es)
ES (1)	ES471239A1 (es)
FR (1)	FR2395998A1 (es)
GB (1)	GB2000508B (es)
IT (1)	IT1105731B (es)
NL (1)	NL7807023A (es)
SE (1)	SE434836B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4430344A (en)	1978-04-08	1984-02-07	Santen Pharmaceutical Co., Ltd.	Antihypertensive 4-thiazolidinecarboxylic acids
US4483861A (en) *	1978-10-31	1984-11-20	Santen Pharmaceutical Co., Ltd.	Antihypertensive sulfur-containing compounds
JPS5572169A (en) *	1978-11-27	1980-05-30	Tanabe Seiyaku Co Ltd	Isoquinoline derivative and its preparation
JPS5683483A (en) *	1979-12-13	1981-07-08	Santen Pharmaceut Co Ltd	Thiazolidine compound
DE3011239A1 (de) *	1980-03-22	1981-10-01	C.H. Boehringer Sohn, 6507 Ingelheim	Substituierte alkylthioacylaminosaeuren, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen
JPS56139455A (en)	1980-04-02	1981-10-30	Santen Pharmaceut Co Ltd	Sulfur-containing acylaminoacid
AU543804B2 (en) *	1980-10-31	1985-05-02	Takeda Chemical Industries Ltd.	Amides having bicyclic substituents on nitrogen
DE3204373A1 (de) *	1982-02-09	1983-08-18	Luitpold-Werk, Chemisch-pharmazeutische Fabrik GmbH & Co, 8000 München	Thiazaspiranderivate, verfahren zu ihrer herstellung und arzneimittel
US4552889A (en) *	1983-06-09	1985-11-12	Eli Lilly And Company	3-Mercaptomethyl-2-oxo-1-pyrrolidine acetic acids and use for hypertension
USD583254S1 (en) *	2007-12-18	2008-12-23	New York & Company, Inc.	Pump container

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2446100C3 (de) *	1974-09-26	1982-01-14	Ludwig Merckle Kg Chem. Pharm. Fabrik, 7902 Blaubeuren	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
AU518147B2 (en) *	1976-12-03	1981-09-17	E.R. Squibb & Sons, Inc.	Derivatives of thiazolidine, thiazine and morpholine carboxylic acids
JPS5455565A (en) *	1977-10-06	1979-05-02	Santen Pharmaceut Co Ltd	Novel thiazolidine derivative

1978
- 1978-06-27 FR FR7819125A patent/FR2395998A1/fr active Granted
- 1978-06-27 IT IT50037/78A patent/IT1105731B/it active
- 1978-06-28 GB GB7828177A patent/GB2000508B/en not_active Expired
- 1978-06-28 SE SE7807335A patent/SE434836B/sv not_active IP Right Cessation
- 1978-06-28 ES ES471239A patent/ES471239A1/es not_active Expired
- 1978-06-29 DE DE2828578A patent/DE2828578C2/de not_active Expired
- 1978-06-29 NL NL7807023A patent/NL7807023A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL7807023A (nl)	1979-01-03
FR2395998B1 (es)	1982-07-23
SE7807335L (sv)	1978-12-30
ES471239A1 (es)	1979-01-16
DE2828578A1 (de)	1979-01-11
GB2000508A (en)	1979-01-10
DE2828578C2 (de)	1983-12-15
GB2000508B (en)	1982-05-19
IT1105731B (it)	1985-11-04
IT7850037A0 (it)	1978-06-27
FR2395998A1 (fr)	1979-01-26

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NL194239C (nl)	2001-10-02	Dialkoxyfosfinolmethylbenzamideverbindingen en farmaceutische preparaten, die deze bevatten.
KR940009528B1 (ko)	1994-10-14	헤테로 고리 화합물의 제조 방법
KR960010346B1 (ko)	1996-07-30	4(3h)-퀴나졸리논 유도체, 이의 제조방법 및 약제학적 조성물
WO1995024397A1 (de)	1995-09-14	3,5-disubstituierte und 3,4,5-trisubstituierte 2-isoxazoline und isoxazole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5258397A (en)	1993-11-02	3-Isoxazoyl derivatives endowed with anticonvulsant activity, procedure for their preparation and their pharmaceutical compositions
SE434836B (sv)	1984-08-20	Tiazolidinforeningar
KR870001144B1 (ko)	1987-06-11	삼환 옥스인돌 카복스아미드 유도체의 제조방법
SI9200240A (en)	1993-06-30	New acylates from imidazole-5-carboxylic acid derivatives and process for their preparation and their use
US4450275A (en)	1984-05-22	Cyclic iminocarboxylic acid derivatives
NL193541C (nl)	2000-01-04	8 Alfa-acylaminoergolinen, werkwijzen voor de bereiding daarvan en preparaten die ze bevatten.
US5434167A (en)	1995-07-18	Imidazolines N-substituted by a biphenylmethyl group, their medical use and the pharmaceutical compositions therefor
FR2684672A1 (fr)	1993-06-11	Derives de pyrimidine, utiles pour le traitement d'etats tels que l'hypertension et l'insuffisance cardiaque, et procede pour leur preparation.
CA1076580A (en)	1980-04-29	2,3,6,7-tetrahydro-5h-pyrrolo-(1,2-a)imidazole compounds
NO823829L (no)	1983-05-18	Fremgangsmaate for fremstilling av terapeutisk virksomme forbindelser.
FI86173B (fi)	1992-04-15	Foerfarande foer framstaellning av farmakologiskt vaerdefulla sulfonamidoetylfoereningar.
US5968967A (en)	1999-10-19	Pyrazolones derivatives
SE408301B (sv)	1979-06-05	Sett att framtella 1-substituerade pyrazoloner -(5)
US5326879A (en)	1994-07-05	Indole derivatives
FR2496666A1 (fr)	1982-06-25	Nouveaux derives de cephalosporine et composition pharmaceutique les contenant
US4317825A (en)	1982-03-02	Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate derivatives
US4103016A (en)	1978-07-25	Antiinflammatory imidazothiazoles and thiazolopyrimidines
IE920334A1 (en)	1992-08-12	THE USE OF THIAZOLO-[2,3-a]-ISOINDOLE DERIVATIVES AS¹ANTIVIRAL PHARMACEUTICALS AND NEW THIAZOLO-[2,3-a]-ISOINDOLE¹DERIVATIVES
JP2794640B2 (ja)	1998-09-10	イミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
Suzuki et al.	1986	Syntheses of 2-Aryl-4-(3-thienyl) imidazole Derivatives with Antiinflammatory Preperties
US4379792A (en)	1983-04-12	Anti-inflammatory composition

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