NO127239B - - Google Patents
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- Publication number
- NO127239B NO127239B NO03753/71*[A NO375371A NO127239B NO 127239 B NO127239 B NO 127239B NO 375371 A NO375371 A NO 375371A NO 127239 B NO127239 B NO 127239B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- aliphatic carboxylic
- carboxylic acid
- denotes
- group
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 (3,5-diamino-2,4,6-triiodobenzoyl)-amino Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 8
- 239000002872 contrast media Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000007487 urography Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 4
- ZAVIHPOYMGHVQY-UHFFFAOYSA-N NC(C(I)=C(C(NCC(O)=O)=O)C(I)=C1N)=C1I Chemical compound NC(C(I)=C(C(NCC(O)=O)=O)C(I)=C1N)=C1I ZAVIHPOYMGHVQY-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ZMMSWDCZEHRVRP-UHFFFAOYSA-N 2-[(3,5-diacetamido-2,4,6-triiodobenzoyl)amino]acetic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(=O)NCC(O)=O)=C1I ZMMSWDCZEHRVRP-UHFFFAOYSA-N 0.000 description 1
- OOUHUXLLFPJKIE-UHFFFAOYSA-N 2-[(3,5-diaminobenzoyl)amino]acetic acid Chemical compound NC1=CC(N)=CC(C(=O)NCC(O)=O)=C1 OOUHUXLLFPJKIE-UHFFFAOYSA-N 0.000 description 1
- MIVUDAUOXJDARR-UHFFFAOYSA-N 2-[(3,5-dinitrobenzoyl)amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MIVUDAUOXJDARR-UHFFFAOYSA-N 0.000 description 1
- PJZXWXFIUIDMBP-UHFFFAOYSA-N 2-[(3,5-dinitrobenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 PJZXWXFIUIDMBP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- XBPNQSRYUZTHDA-UHFFFAOYSA-N OC(CNC(C(C(I)=C(C(I)=C1NC=O)NC=O)=C1I)=O)=O Chemical compound OC(CNC(C(C(I)=C(C(I)=C1NC=O)NC=O)=C1I)=O)=O XBPNQSRYUZTHDA-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Structures Of Non-Positive Displacement Pumps (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62696567A | 1967-03-30 | 1967-03-30 | |
| US639315A US3888846A (en) | 1967-03-30 | 1967-05-18 | Process for 2(2-(1,3-diazacycloalk-2-enyl))benzophenone derivatives and 1,3-diazacycloalkenyl(2,1-a)isoindole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127239B true NO127239B (https=) | 1973-05-28 |
Family
ID=27090306
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1212/68A NO124111B (https=) | 1967-03-30 | 1968-03-29 | |
| NO03753/71*[A NO127239B (https=) | 1967-03-30 | 1971-10-12 | |
| NO03752/71*[A NO127238B (https=) | 1967-03-30 | 1971-10-12 | |
| NO03755/71*[A NO127351B (https=) | 1967-03-30 | 1971-10-12 | |
| NO03754/71*[A NO127350B (https=) | 1967-03-30 | 1971-10-12 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1212/68A NO124111B (https=) | 1967-03-30 | 1968-03-29 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03752/71*[A NO127238B (https=) | 1967-03-30 | 1971-10-12 | |
| NO03755/71*[A NO127351B (https=) | 1967-03-30 | 1971-10-12 | |
| NO03754/71*[A NO127350B (https=) | 1967-03-30 | 1971-10-12 |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS4843360B1 (https=) |
| ES (1) | ES352173A1 (https=) |
| IE (1) | IE31999B1 (https=) |
| IL (1) | IL29651A (https=) |
| MY (1) | MY7300459A (https=) |
| NO (5) | NO124111B (https=) |
| SE (1) | SE346318B (https=) |
| YU (1) | YU33929B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50125392U (https=) * | 1974-03-30 | 1975-10-14 |
-
1968
- 1968-03-18 IL IL29651A patent/IL29651A/en unknown
- 1968-03-27 SE SE4081/68A patent/SE346318B/xx unknown
- 1968-03-29 YU YU717/68A patent/YU33929B/xx unknown
- 1968-03-29 IE IE366/68A patent/IE31999B1/xx unknown
- 1968-03-29 NO NO1212/68A patent/NO124111B/no unknown
-
1969
- 1969-05-19 ES ES352173A patent/ES352173A1/es not_active Expired
-
1970
- 1970-08-03 JP JP45067352A patent/JPS4843360B1/ja active Pending
-
1971
- 1971-10-12 NO NO03753/71*[A patent/NO127239B/no unknown
- 1971-10-12 NO NO03752/71*[A patent/NO127238B/no unknown
- 1971-10-12 NO NO03755/71*[A patent/NO127351B/no unknown
- 1971-10-12 NO NO03754/71*[A patent/NO127350B/no unknown
-
1973
- 1973-02-09 JP JP48016353A patent/JPS5017479B1/ja active Pending
- 1973-12-30 MY MY459/73A patent/MY7300459A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES352173A1 (es) | 1969-10-01 |
| IL29651A (en) | 1972-07-26 |
| NO124111B (https=) | 1972-03-06 |
| YU71768A (en) | 1978-02-28 |
| YU33929B (en) | 1978-09-08 |
| IE31999B1 (en) | 1973-03-07 |
| JPS4843360B1 (https=) | 1973-12-18 |
| MY7300459A (en) | 1973-12-31 |
| NO127350B (https=) | 1973-06-12 |
| JPS5017479B1 (https=) | 1975-06-20 |
| IE31999L (en) | 1968-09-30 |
| NO127351B (https=) | 1973-06-12 |
| NO127238B (https=) | 1973-05-28 |
| SE346318B (https=) | 1972-07-03 |
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