NO117678B - - Google Patents
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- Publication number
- NO117678B NO117678B NO162909A NO16290966A NO117678B NO 117678 B NO117678 B NO 117678B NO 162909 A NO162909 A NO 162909A NO 16290966 A NO16290966 A NO 16290966A NO 117678 B NO117678 B NO 117678B
- Authority
- NO
- Norway
- Prior art keywords
- weight
- parts
- theophylline
- dialkylxanthine
- reaction
- Prior art date
Links
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical group O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 28
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229960000278 theophylline Drugs 0.000 claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000003973 alkyl amines Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 6
- ZWBASWPKNUWUSZ-UHFFFAOYSA-N 1,3-dimethyl-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC([N+]([O-])=O)=N2 ZWBASWPKNUWUSZ-UHFFFAOYSA-N 0.000 claims description 4
- SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 claims description 4
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229960004559 theobromine Drugs 0.000 claims description 3
- 235000013312 flour Nutrition 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000005887 phenylation reaction Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000007859 condensation product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- RLANKEDHRWMNRO-UHFFFAOYSA-M oxtriphylline Chemical compound C[N+](C)(C)CCO.O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 RLANKEDHRWMNRO-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229960001231 choline Drugs 0.000 description 8
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 8
- -1 choline Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JPKKMFOXWKNEEN-UHFFFAOYSA-N 2-methylcholine Chemical compound CC(O)C[N+](C)(C)C JPKKMFOXWKNEEN-UHFFFAOYSA-N 0.000 description 5
- QUNWUDVFRNGTCO-UHFFFAOYSA-N 1,7-dimethylxanthine Chemical compound N1C(=O)N(C)C(=O)C2=C1N=CN2C QUNWUDVFRNGTCO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Natural products O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B7/00—Shotgun ammunition
- F42B7/02—Cartridges, i.e. cases with propellant charge and missile
- F42B7/08—Wads, i.e. projectile or shot carrying devices, therefor
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Sampling And Sample Adjustment (AREA)
- Table Devices Or Equipment (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US459598A US3285174A (en) | 1965-05-28 | 1965-05-28 | Wad and shot protector device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117678B true NO117678B (de) | 1969-09-08 |
Family
ID=23825425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162909A NO117678B (de) | 1965-05-28 | 1966-05-06 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3285174A (de) |
| BE (1) | BE681727A (de) |
| DE (1) | DE1578187B1 (de) |
| GB (1) | GB1148075A (de) |
| NO (1) | NO117678B (de) |
| SE (1) | SE325493B (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394654A (en) * | 1965-10-14 | 1968-07-30 | Kawaguchiya Firearms | Cartridge |
| US3788224A (en) * | 1966-06-24 | 1974-01-29 | Federal Cartridge Corp | Nested wad column and method of shot shell loading |
| US3402664A (en) * | 1966-09-13 | 1968-09-24 | John E. Cramer | Shot holder and wad for shot shells |
| US3487779A (en) * | 1968-01-17 | 1970-01-06 | Grover E Hendricks | Shot shell |
| US3516360A (en) * | 1968-03-27 | 1970-06-23 | Olin Mathieson | Shot container |
| US3565010A (en) * | 1968-06-10 | 1971-02-23 | Remington Arms Co Inc | Plastic wad column |
| GB1226233A (de) * | 1969-02-12 | 1971-03-24 | ||
| US3724378A (en) * | 1969-05-13 | 1973-04-03 | R Knight | Shot concentrator |
| US3721194A (en) * | 1970-04-13 | 1973-03-20 | C Weston | Diversifying the shooting characteristics of shotguns |
| US3707915A (en) * | 1970-10-19 | 1973-01-02 | J Kerzman | Wad assembly for shotgun shell |
| US3750579A (en) * | 1971-09-09 | 1973-08-07 | L Bellington | Shotgun shell wad |
| US4151799A (en) * | 1977-09-23 | 1979-05-01 | Jackson John W | Wad for shotgun shell |
| US4220090A (en) * | 1978-09-05 | 1980-09-02 | Fackler David G | Shot wad column |
| US4291625A (en) * | 1979-03-02 | 1981-09-29 | Stagg Jr George A | Shot gun shell construction |
| US4676170A (en) * | 1984-07-16 | 1987-06-30 | Non-Toxic Components, Inc. | One-piece wad structure adapted for reloading of hard shot |
| US4782759A (en) * | 1987-06-30 | 1988-11-08 | Hawk Walter J | Dual sealed composite wad structure |
| US4864934A (en) * | 1988-12-12 | 1989-09-12 | Olin Corporation | Industrial shotshell having a load-stabilizing assembly |
| US6161482A (en) * | 1998-08-18 | 2000-12-19 | Clark; George D. | Multi-disk shell and wad |
| US8800449B2 (en) | 2008-10-27 | 2014-08-12 | Ra Brands, L.L.C. | Wad with ignition chamber |
| WO2010062584A1 (en) * | 2008-10-27 | 2010-06-03 | Ra Brands, L.L.C | Wad with ignition chamber |
| US8555785B2 (en) * | 2009-02-02 | 2013-10-15 | Ra Brands, L.L.C. | Shotshell wad with shot confinement feature |
| US8807040B2 (en) | 2011-07-07 | 2014-08-19 | James Y. Menefee, III | Cartridge for multiplex load |
| US9052172B2 (en) | 2012-05-25 | 2015-06-09 | James Curtis Whitworth | Firearm cleaning shell |
| US9194674B2 (en) | 2012-05-25 | 2015-11-24 | James Curtis Whitworth | Firearm cleaning shell |
| US10012466B2 (en) | 2015-03-06 | 2018-07-03 | James Curtis Whitworth | Firearm bore cleaning device |
| US9664487B2 (en) * | 2015-07-06 | 2017-05-30 | James Curtis Whitworth | Firearm cleaning shell |
| US20230228544A1 (en) * | 2022-01-17 | 2023-07-20 | Seismic Ammunition, Inc. | Firearm projectile |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1116967A (fr) * | 1954-12-31 | 1956-05-15 | Bourre semi-pneumatique en matière plastique pour cartouches de chasse | |
| FR1255572A (fr) * | 1960-03-09 | 1961-03-10 | Concentrateur spécial pour cartouches de chasse à longue portée | |
| FR1257337A (fr) * | 1960-05-07 | 1961-03-31 | Bourre de sécurité à expansion automatique en matière plastique | |
| US3055301A (en) * | 1961-03-13 | 1962-09-25 | Olin Mathieson | Ammunition |
| US3217648A (en) * | 1962-10-08 | 1965-11-16 | Remington Arms Co Inc | Combination wad column and shot liner |
| US3180265A (en) * | 1963-03-01 | 1965-04-27 | R & K Plastic Ind Co | Shot shell wad and container |
-
1965
- 1965-05-28 US US459598A patent/US3285174A/en not_active Expired - Lifetime
-
1966
- 1966-05-04 GB GB19720/66A patent/GB1148075A/en not_active Expired
- 1966-05-06 NO NO162909A patent/NO117678B/no unknown
- 1966-05-27 SE SE07284/66A patent/SE325493B/xx unknown
- 1966-05-27 BE BE681727D patent/BE681727A/xx not_active IP Right Cessation
- 1966-05-27 DE DE19661578187 patent/DE1578187B1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE681727A (de) | 1966-11-28 |
| DE1578187B1 (de) | 1971-06-24 |
| GB1148075A (en) | 1969-04-10 |
| US3285174A (en) | 1966-11-15 |
| SE325493B (de) | 1970-06-29 |
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