NO117129B - - Google Patents

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Info

Publication number: NO117129B
Authority: NO; Norway
Prior art keywords: solution; evaporated; dryness; isopropanol; chloroform
Prior art date: 1966-01-25

Application number

NO166551A

Other languages

English (en)

Norwegian (no)

Inventor

N Gruenfeld

Original Assignee

Geigy Ag J R

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.)

1966-01-25

Filing date

1967-01-24

Publication date

1969-07-07

1967-01-24 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1969-07-07 Publication of NO117129B publication Critical patent/NO117129B/no

Links

150000001875 compounds Chemical class 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000012458 free base Substances 0.000 claims description 6
150000002460 imidazoles Chemical class 0.000 claims description 6
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000000243 solution Substances 0.000 description 102
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 76
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
-1 e.g. hydrochloric Chemical class 0.000 description 19
238000001953 recrystallisation Methods 0.000 description 19
238000010992 reflux Methods 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
239000000126 substance Substances 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
239000007858 starting material Substances 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 12
239000002026 chloroform extract Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000007792 addition Methods 0.000 description 11
239000000725 suspension Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000012491 analyte Substances 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000007017 scission Effects 0.000 description 5
PWZKESLISFPGHR-UHFFFAOYSA-N (2-chlorophenyl)cyanamide Chemical compound ClC1=CC=CC=C1NC#N PWZKESLISFPGHR-UHFFFAOYSA-N 0.000 description 4
BVVSUFVLGBJYOR-UHFFFAOYSA-N (2-methyl-1,3-dioxolan-2-yl)methanamine Chemical compound NCC1(C)OCCO1 BVVSUFVLGBJYOR-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
IXDJNJHGOQUYCG-UHFFFAOYSA-N 1-(2-methyl-1,3-dioxolan-2-yl)ethanamine Chemical compound CC(N)C1(C)OCCO1 IXDJNJHGOQUYCG-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002540 isothiocyanates Chemical class 0.000 description 3
229940046892 lead acetate Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
ACOLGRUIHSRLDA-UHFFFAOYSA-N 1-phenylimidazol-2-amine Chemical compound N=C1NC=CN1C1=CC=CC=C1 ACOLGRUIHSRLDA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
MLPMLUYPZZEGPJ-UHFFFAOYSA-N [2-chloro-5-(trifluoromethyl)phenyl]cyanamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(NC#N)=C1 MLPMLUYPZZEGPJ-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
FHJDVUALGCLJJO-UHFFFAOYSA-N 1-(4-fluorophenyl)imidazol-2-amine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)N1C(=NC=C1)N FHJDVUALGCLJJO-UHFFFAOYSA-N 0.000 description 1
JRNCBRIPJQMSDN-UHFFFAOYSA-N 1-(4-methoxyphenyl)imidazol-2-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=NC=C1 JRNCBRIPJQMSDN-UHFFFAOYSA-N 0.000 description 1
KHTMKXDMVYHDSY-UHFFFAOYSA-N 1-chloro-2-isothiocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(N=C=S)=C1 KHTMKXDMVYHDSY-UHFFFAOYSA-N 0.000 description 1
QLWOUBCORTYSPP-UHFFFAOYSA-N 1h-imidazol-1-ium;hydroxide Chemical class O.C1=CNC=N1 QLWOUBCORTYSPP-UHFFFAOYSA-N 0.000 description 1
STMRGLKPBJVVEG-UHFFFAOYSA-N 2-(2-oxopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC(=O)C)C(=O)C2=C1 STMRGLKPBJVVEG-UHFFFAOYSA-N 0.000 description 1
NKPDEEQLUDNJPD-UHFFFAOYSA-N 2-(3-oxobutan-2-yl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(C)C(C)=O)C(=O)C2=C1 NKPDEEQLUDNJPD-UHFFFAOYSA-N 0.000 description 1
BFHRMYJJIMKAFV-UHFFFAOYSA-N 2-iodoguanidine Chemical compound NC(N)=NI BFHRMYJJIMKAFV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
DSPIJMWCUJARNS-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)N1C(=NC=C1)N Chemical compound Cl.C1(=CC=CC=C1)N1C(=NC=C1)N DSPIJMWCUJARNS-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
FRWSMFYOXZLADY-UHFFFAOYSA-N n-(2-chlorophenyl)-1h-imidazol-2-amine Chemical compound ClC1=CC=CC=C1NC1=NC=CN1 FRWSMFYOXZLADY-UHFFFAOYSA-N 0.000 description 1
JWFHUXMTNRDYCZ-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-1h-imidazol-2-amine Chemical compound ClC1=CC=CC=C1CNC1=NC=CN1 JWFHUXMTNRDYCZ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000009738 saturating Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000028327 secretion Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960002178 thiamazole Drugs 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1

Classifications

- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
- C07D233/88—Nitrogen atoms, e.g. allantoin

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO166551A 1966-01-25 1967-01-24 NO117129B (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US52282966A	1966-01-25	1966-01-25

Publications (1)

Publication Number	Publication Date
NO117129B true NO117129B (2)	1969-07-07

Family

ID=24082557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO166551A NO117129B (2)	1966-01-25	1967-01-24

Country Status (14)

Country	Link
US (1)	US3459763A (2)
AT (1)	AT262997B (2)
BE (1)	BE693079A (2)
CH (1)	CH474522A (2)
DE (1)	DE1695005A1 (2)
DK (1)	DK121302B (2)
ES (1)	ES336020A1 (2)
FR (2)	FR1508888A (2)
GB (1)	GB1131191A (2)
GR (1)	GR36359B (2)
IL (1)	IL27312A (2)
NL (1)	NL6701100A (2)
NO (1)	NO117129B (2)
SE (1)	SE339475B (2)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3700685A (en) *	1970-05-15	1972-10-24	Merck & Co Inc	Nitroimidazole derivatives
US3859302A (en) *	1973-02-05	1975-01-07	Monsanto Co	Preparation of 2-imino-imidazole derivatives
FR2269341B1 (2) *	1974-04-30	1978-07-28	Castaigne Sa
US4195092A (en) *	1977-12-27	1980-03-25	Eli Lilly And Company	2-(Substituted amino)-N-(3-substituted phenyl)-2-imidazoline-1-carbothioamides
EP0656210A1 (en) *	1993-11-19	1995-06-07	Takeda Chemical Industries, Ltd.	Imidazole derivatives as glutaminose inhibitors
ES2160700T3 (es) *	1994-01-24	2001-11-16	Allergan Sales Inc	Derivados aromaticos de 2-amino-imidazol como agonistas del adrenorreceptor alfa-2a.
US5922751A (en) *	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
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1966
- 1966-01-25 US US522829A patent/US3459763A/en not_active Expired - Lifetime
1967
- 1967-01-23 CH CH95167A patent/CH474522A/de not_active IP Right Cessation
- 1967-01-24 BE BE693079D patent/BE693079A/xx unknown
- 1967-01-24 DE DE19671695005 patent/DE1695005A1/de active Pending
- 1967-01-24 NL NL6701100A patent/NL6701100A/xx unknown
- 1967-01-24 DK DK42267AA patent/DK121302B/da unknown
- 1967-01-24 GB GB3518/67A patent/GB1131191A/en not_active Expired
- 1967-01-24 SE SE01034/67A patent/SE339475B/xx unknown
- 1967-01-24 IL IL27312A patent/IL27312A/en unknown
- 1967-01-24 ES ES0336020A patent/ES336020A1/es not_active Expired
- 1967-01-24 GR GR670136359A patent/GR36359B/el unknown
- 1967-01-24 NO NO166551A patent/NO117129B/no unknown
- 1967-01-24 AT AT68467A patent/AT262997B/de active
- 1967-01-25 FR FR92418A patent/FR1508888A/fr not_active Expired
- 1967-04-21 FR FR103671A patent/FR6337M/fr not_active Expired

Also Published As

Publication number	Publication date
ES336020A1 (es)	1967-12-16
GR36359B (el)	1969-02-03
FR6337M (2)	1968-09-30
FR1508888A (fr)	1968-01-05
DE1695005A1 (de)	1971-02-25
AT262997B (de)	1968-07-10
US3459763A (en)	1969-08-05
BE693079A (2)	1967-07-24
CH474522A (de)	1969-06-30
SE339475B (2)	1971-10-11
NL6701100A (2)	1967-07-26
IL27312A (en)	1971-01-28
GB1131191A (en)	1968-10-23
DK121302B (da)	1971-10-04

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EP0328026B1 (de)	1993-04-28	Substituierte Pyrrole
US3161654A (en)	1964-12-15	alpha-(1-aroyl-3-indolyl) alkanoic acids
NO124032B (2)	1972-02-21
DE1695093A1 (de)	1970-12-10	Neue Imidazolderivate
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NO170987B (no)	1992-09-28	Fremgangsmaate for avsvovling av jern
SU1362402A3 (ru)	1987-12-23	Способ получени производных имидазола или их солей с кислотами
US4544655A (en)	1985-10-01	Antiinflammatory, analgesic, and antirheumatic 4-hydroxy-2-methyl-n-(2-pyridyl)-6-trifluoromethyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide, corresponding compositions, and 3-carboxylic acid lower alkyl ester intermediates
NO117366B (2)	1969-08-04
US3847934A (en)	1974-11-12	7-(imidazolinyl-(2)-amino)-indazoles
US3299090A (en)	1967-01-17	Nitroimidazoles
US3383382A (en)	1968-05-14	N-amino-iminodibenzyl
NO120370B (2)	1970-10-12
EP0025501B1 (de)	1982-12-29	Neue N-Aminoalkylindol-Derivate und ihre Salze; Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
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