JPH0136474B2 - - Google Patents

Info

Publication number: JPH0136474B2
Authority: JP; Japan
Prior art keywords: bis; amino; group; compounds; hydroxy
Prior art date: 1980-01-31
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.): Expired

Application number

JP56012257A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56127373A (en

Inventor

Sobaku Mirosu

Ranganasan Ramanchandoran

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.)

YUNIBAASHITEI OBU KARIFUORUNIA

Original Assignee

YUNIBAASHITEI OBU KARIFUORUNIA

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.)

1980-01-31

Filing date

1981-01-31

Publication date

1989-07-31

1981-01-31 Application filed by YUNIBAASHITEI OBU KARIFUORUNIA filed Critical YUNIBAASHITEI OBU KARIFUORUNIA

1981-10-06 Publication of JPS56127373A publication Critical patent/JPS56127373A/ja

1989-07-31 Publication of JPH0136474B2 publication Critical patent/JPH0136474B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
GTPWYANJPNGAAY-UHFFFAOYSA-N 1,3-dioxepine Chemical compound C1OC=CC=CO1 GTPWYANJPNGAAY-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 2
OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 claims 1
239000002872 contrast media Substances 0.000 description 37
229910052757 nitrogen Inorganic materials 0.000 description 30
239000000047 product Substances 0.000 description 30
238000000034 method Methods 0.000 description 19
-1 5-(N-methylacetamido)triiodobenzoyl Chemical class 0.000 description 18
239000000203 mixture Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
125000003277 amino group Chemical group 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
150000002118 epoxides Chemical class 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000012267 brine Substances 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
230000008569 process Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
150000001540 azides Chemical class 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
231100000053 low toxicity Toxicity 0.000 description 4
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 4
239000012038 nucleophile Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
238000000746 purification Methods 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
BXRMFUZPBYHYSM-PHDIDXHHSA-N (5s,6r)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol Chemical compound CC1(C)OC[C@@H](N)[C@H](O)CO1 BXRMFUZPBYHYSM-PHDIDXHHSA-N 0.000 description 3
ATZGUXPLGMKHOR-UHFFFAOYSA-N 2,2-dimethyl-4,7-dihydro-1,3-dioxepine Chemical compound CC1(C)OCC=CCO1 ATZGUXPLGMKHOR-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
238000006735 epoxidation reaction Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 3
229960004647 iopamidol Drugs 0.000 description 3
125000005647 linker group Chemical group 0.000 description 3
229960000554 metrizamide Drugs 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002243 precursor Substances 0.000 description 3
230000002285 radioactive effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
CZLMRJZAHXYRIX-UHFFFAOYSA-N 1,3-dioxepane Chemical compound C1CCOCOC1 CZLMRJZAHXYRIX-UHFFFAOYSA-N 0.000 description 2
YLJAKJSGUDBOHG-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I YLJAKJSGUDBOHG-UHFFFAOYSA-N 0.000 description 2
JOWXBGIZDALBJW-UHFFFAOYSA-N 3h-dioxepine Chemical compound C1OOC=CC=C1 JOWXBGIZDALBJW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 description 2
150000000129 dioxepanes Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000003204 osmotic effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
238000001308 synthesis method Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
PMLGQXIKBPFHJZ-IMJSIDKUSA-N (2r,3s)-3-aminobutane-1,2,4-triol Chemical compound OC[C@H](N)[C@@H](O)CO PMLGQXIKBPFHJZ-IMJSIDKUSA-N 0.000 description 1
HGVUWQBXZZWUGD-REOHCLBHSA-N (2s)-2-hydroxypropanoyl chloride Chemical compound C[C@H](O)C(Cl)=O HGVUWQBXZZWUGD-REOHCLBHSA-N 0.000 description 1
PMLGQXIKBPFHJZ-QWWZWVQMSA-N (2s,3r)-3-aminobutane-1,2,4-triol Chemical compound OC[C@@H](N)[C@H](O)CO PMLGQXIKBPFHJZ-QWWZWVQMSA-N 0.000 description 1
DSZCIGBZTXFVFQ-OTTPZQCVSA-N (3R,4R,5S,6R)-2-[4,6-diiodo-2,3-bis[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound IC1=CC(=C(C(=C1C1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)I DSZCIGBZTXFVFQ-OTTPZQCVSA-N 0.000 description 1
RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical class IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
GRMNJXQBRPJVQV-UHFFFAOYSA-N 2,3-dihydroxybutanediamide Chemical compound NC(=O)C(O)C(O)C(N)=O GRMNJXQBRPJVQV-UHFFFAOYSA-N 0.000 description 1
UEQABUISLVYURQ-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I UEQABUISLVYURQ-UHFFFAOYSA-N 0.000 description 1
JYSFGKGZDKMHDN-UHFFFAOYSA-N 2-amino-1,3-dioxepan-5-ol Chemical compound NC1OCCC(O)CO1 JYSFGKGZDKMHDN-UHFFFAOYSA-N 0.000 description 1
LDOMKUVUXZRECL-UHFFFAOYSA-N 2-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(C(O)=O)C=CC=C1C(O)=O LDOMKUVUXZRECL-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
GEKNCWQQNMEIMS-UHFFFAOYSA-N 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane Chemical compound C1OC(C)(C)OCC2OC21 GEKNCWQQNMEIMS-UHFFFAOYSA-N 0.000 description 1
NTVCIOGUJHBVBO-UHFFFAOYSA-N 4,5-dihydro-3h-dioxepine Chemical compound C1COOC=CC1 NTVCIOGUJHBVBO-UHFFFAOYSA-N 0.000 description 1
QZOXBDVVVOIOEY-UHFFFAOYSA-N 4-aminobutane-1,1,1-triol Chemical compound NCCCC(O)(O)O QZOXBDVVVOIOEY-UHFFFAOYSA-N 0.000 description 1
MYWMLEMKOKPNAP-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I MYWMLEMKOKPNAP-UHFFFAOYSA-N 0.000 description 1
FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 description 1
AGNSCOWWQUDEGE-UHFFFAOYSA-N 6-amino-1,3-dioxepan-5-ol Chemical compound NC1COCOCC1O AGNSCOWWQUDEGE-UHFFFAOYSA-N 0.000 description 1
BXRMFUZPBYHYSM-UHFFFAOYSA-N 6-amino-2,2-dimethyl-1,3-dioxepan-5-ol Chemical compound CC1(C)OCC(N)C(O)CO1 BXRMFUZPBYHYSM-UHFFFAOYSA-N 0.000 description 1
QPOQUXLUIBFXSQ-UHFFFAOYSA-N 6-amino-2,2-dipropyl-1,3-dioxepan-5-ol Chemical compound CCCC1(CCC)OCC(N)C(O)CO1 QPOQUXLUIBFXSQ-UHFFFAOYSA-N 0.000 description 1
AVIVPMVPRPJDNN-UHFFFAOYSA-N 6-amino-2-(methoxymethyl)-2-methyl-1,3-dioxepan-5-ol Chemical compound COCC1(C)OCC(N)C(O)CO1 AVIVPMVPRPJDNN-UHFFFAOYSA-N 0.000 description 1
CAIXQJFXZPCEKU-UHFFFAOYSA-N 6-amino-2-benzyl-1,3-dioxepan-5-ol Chemical compound O1CC(O)C(N)COC1CC1=CC=CC=C1 CAIXQJFXZPCEKU-UHFFFAOYSA-N 0.000 description 1
SLOOQCDTPVGZOA-UHFFFAOYSA-N 6-amino-2-ethyl-2-methyl-1,3-dioxepan-5-ol Chemical compound CCC1(C)OCC(N)C(O)CO1 SLOOQCDTPVGZOA-UHFFFAOYSA-N 0.000 description 1
FCGDGJFDVZUVOR-UHFFFAOYSA-N 6-amino-2-phenyl-1,3-dioxepan-5-ol Chemical compound O1CC(O)C(N)COC1C1=CC=CC=C1 FCGDGJFDVZUVOR-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010063659 Aversion Diseases 0.000 description 1
241000248447 Blepharisma Species 0.000 description 1
ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
101000780208 Homo sapiens Long-chain-fatty-acid-CoA ligase 4 Proteins 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
102100034319 Long-chain-fatty-acid-CoA ligase 4 Human genes 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009227 behaviour therapy Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229960005423 diatrizoate Drugs 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
JVBYPWNCEXAUHU-UHFFFAOYSA-N dioxepan-3-ol Chemical class OC1CCCCOO1 JVBYPWNCEXAUHU-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005188 flotation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000004966 inorganic peroxy acids Chemical class 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002372 labelling Methods 0.000 description 1
210000003140 lateral ventricle Anatomy 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
230000004089 microcirculation Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000010494 opalescence Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
150000002971 pentose derivatives Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP1225781A 1980-01-31 1981-01-31 Novel amino-dioxepane intermediate for synthesizing novel nonionic contrast agent Granted JPS56127373A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11715180A	1980-01-31	1980-01-31

Publications (2)

Publication Number	Publication Date
JPS56127373A JPS56127373A (en)	1981-10-06
JPH0136474B2 true JPH0136474B2 (de)	1989-07-31

Family

ID=22371223

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP1225781A Granted JPS56127373A (en)	1980-01-31	1981-01-31	Novel amino-dioxepane intermediate for synthesizing novel nonionic contrast agent
JP62133547A Granted JPS6360958A (ja)	1980-01-31	1987-05-30	非イオン造影剤合成用中間体

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP62133547A Granted JPS6360958A (ja)	1980-01-31	1987-05-30	非イオン造影剤合成用中間体

Country Status (1)

Country	Link
JP (2)	JPS56127373A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6133461A (en)	1995-09-26	2000-10-17	Japan Tobacco Inc.	Process for producing amide derivatives and intermediates therefor
WO1997011938A1 (en) *	1995-09-26	1997-04-03	Japan Tobacco Inc.	Process for producing amide derivatives and intermediate compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2628517C2 (de) *	1976-06-23	1985-02-21	Schering AG, 1000 Berlin und 4709 Bergkamen	Dicarbonsäure-bis(3,5-dicarbamoyl-2,4,6-trijodanilid)-Verbindungen, Verfahren zu ihrer Herstellung und Röntgenkontrastmittel
IT1193211B (it) *	1979-08-09	1988-06-15	Bracco Ind Chimica Spa	Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono
DE3001292A1 (de) *	1980-01-11	1981-07-16	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Nichtionische 5-c-substituierte 2,4,6-trijod-isophthalsaeure-derivate

1981
- 1981-01-31 JP JP1225781A patent/JPS56127373A/ja active Granted
1987
- 1987-05-30 JP JP62133547A patent/JPS6360958A/ja active Granted

Also Published As

Publication number	Publication date
JPS6360958A (ja)	1988-03-17
JPS56127373A (en)	1981-10-06
JPH0129785B2 (de)	1989-06-14

Publication	Publication Date	Title
US4341756A (en)	1982-07-27	Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media
US7087768B2 (en)	2006-08-08	Fumagillol derivatives and preparing method thereof
KR100759144B1 (ko)	2007-09-14	1,2,4-트리옥솔란 항말라리아제
EP0889042B1 (de)	2004-05-06	Radicicolderivate
FR2503702A1 (fr)	1982-10-15	Nouveaux cycloalcane-amides a substituants adjacents, doues de proprietes analgesiques et compositions pharmaceutiques les contenant
EP0499501B1 (de)	1998-08-19	Neue makrocyclische Stickstoff-Liganden, Verfahren zu ihrer Herstellung, Metallkomplexe, diagnostische und therapeutische Zusammensetzungen
JPS6094960A (ja)	1985-05-28	新規ニトロキシル化合物、その製法およびこれを含有するｎｍｒ診断剤
US4439613A (en)	1984-03-27	Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media
US3801636A (en)	1974-04-02	3,4,5-tri-substituted cinnamides
PL153184B1 (en)	1991-03-29	Method for manufacturing new heterocyclic derivatives of propane
WO2007074091A2 (en)	2007-07-05	Epoxide intermediate in the tamiflu synthesis
KR0178956B1 (ko)	1999-03-20	항균성 페넴 에스테르 유도체
JPH0136474B2 (de)	1989-07-31
FR2584073A1 (fr)	1987-01-02	Analogues d'amino-prostaglandines a substituant 5,6-epoxy-7-oxabicycloheptane, utilisables pour le traitement des thromboses
KR100832047B1 (ko)	2008-05-27	퍼옥사이드 유도체를 함유하는 이중 분자, 이 분자의 합성 방법 및 치료적 용도
CA1271481A (en)	1990-07-10	Process for the preparation of novel isoxazole derivatives
JP2899433B2 (ja)	1999-06-02	アルキレンジオキシベンゼン誘導体およびそれを有効成分とする抗不安薬
EP0298583B1 (de)	1991-08-21	Aromatische Thioäther
KR100781403B1 (ko)	2007-12-03	항해수성 1,3-디옥솔란
US4389526A (en)	1983-06-21	Intermediates and synthesis of 2-amino-2-deoxytetritols
CA2491989C (fr)	2012-03-20	Composes a activite anti-parasitaire et medicaments les renfermant
JP3165409B2 (ja)	2001-05-14	アルキレンジオキシベンゼン誘導体を有効成分とする抗不安薬
FR2499569A1 (fr)	1982-08-13	Nouveaux derives de 1-benzyl- 4-(4-(2-pyrimidinylamino)benzyl)-2,3- dioxopiperazines, leurs sels, un procede de preparation de ces derives et sels et un agent carcinostatique les contenant
JPS6330490A (ja)	1988-02-09	アミノベンゾキサジノリフアマイシン誘導体
BE640084A (de)