NO118335B - - Google Patents

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Info

Publication number: NO118335B
Authority: NO; Norway
Prior art keywords: water; formula; alcohol; soluble; para
Prior art date: 1967-10-18

Application number

NO17017167A

Other languages

English (en)

Norwegian (no)

Inventor

K Yamaguchi

Original Assignee

Asia Sekiyu Kabushiki Kaisha

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.)

1967-10-18

Filing date

1967-10-18

Publication date

1969-12-15

1967-10-18 Application filed by Asia Sekiyu Kabushiki Kaisha filed Critical Asia Sekiyu Kabushiki Kaisha

1967-10-18 Priority to NO17017167A priority Critical patent/NO118335B/no

1968-10-17 Priority to DK500068A priority patent/DK120323B/da

1969-12-15 Publication of NO118335B publication Critical patent/NO118335B/no

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 5
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims description 4
239000003589 local anesthetic agent Substances 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
229960002327 chloral hydrate Drugs 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
230000003444 anaesthetic effect Effects 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
150000001875 compounds Chemical class 0.000 description 10
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 7
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
229960004919 procaine Drugs 0.000 description 4
239000000126 substance Substances 0.000 description 4
FLXRAHVGFGGXQD-UHFFFAOYSA-N 2-(diethylamino)ethyl 4-[3-[[4-[2-(diethylamino)ethoxycarbonyl]phenyl]carbamoyloxy]propoxycarbonylamino]benzoate Chemical compound C1=CC(C(=O)OCCN(CC)CC)=CC=C1NC(=O)OCCCOC(=O)NC1=CC=C(C(=O)OCCN(CC)CC)C=C1 FLXRAHVGFGGXQD-UHFFFAOYSA-N 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229960004050 aminobenzoic acid Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 2
229960000244 procainamide Drugs 0.000 description 2
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
229960001309 procaine hydrochloride Drugs 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
VWZAGCZUPZKTET-UHFFFAOYSA-N 3-(dibutylamino)propyl 4-aminobenzoate;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCN(CCCC)CCCOC(=O)C1=CC=C(N)C=C1.CCCCN(CCCC)CCCOC(=O)C1=CC=C(N)C=C1 VWZAGCZUPZKTET-UHFFFAOYSA-N 0.000 description 1
HQFWVSGBVLEQGA-UHFFFAOYSA-N 4-aminobenzoic acid 3-(dibutylamino)propyl ester Chemical compound CCCCN(CCCC)CCCOC(=O)C1=CC=C(N)C=C1 HQFWVSGBVLEQGA-UHFFFAOYSA-N 0.000 description 1
KKHMQRRQQBALFL-UHFFFAOYSA-N 4-isocyanatobenzoic acid Chemical compound OC(=O)C1=CC=C(N=C=O)C=C1 KKHMQRRQQBALFL-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
-1 aliphatic alcohols Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960003369 butacaine Drugs 0.000 description 1
229960004598 butacaine sulfate Drugs 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical class O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
238000002690 local anesthesia Methods 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO17017167A 1967-10-18 1967-10-18 NO118335B (da)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
NO17017167A NO118335B (da)	1967-10-18	1967-10-18
DK500068A DK120323B (da)	1967-10-18	1968-10-17	Luftrensningsanlæg.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NO17017167A NO118335B (da)	1967-10-18	1967-10-18

Publications (1)

Publication Number	Publication Date
NO118335B true NO118335B (da)	1969-12-15

Family

ID=19910265

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO17017167A NO118335B (da)	1967-10-18	1967-10-18

Country Status (2)

Country	Link
DK (1)	DK120323B (da)
NO (1)	NO118335B (da)

1967
- 1967-10-18 NO NO17017167A patent/NO118335B/no unknown
1968
- 1968-10-17 DK DK500068A patent/DK120323B/da unknown

Also Published As

Publication number	Publication date
DK120323B (da)	1971-05-10

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