NO127359B - - Google Patents
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- Publication number
- NO127359B NO127359B NO04205/68A NO420568A NO127359B NO 127359 B NO127359 B NO 127359B NO 04205/68 A NO04205/68 A NO 04205/68A NO 420568 A NO420568 A NO 420568A NO 127359 B NO127359 B NO 127359B
- Authority
- NO
- Norway
- Prior art keywords
- hydrochloride
- biguanide
- filtered
- mixture
- insulin
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 229940123208 Biguanide Drugs 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000012458 free base Substances 0.000 claims description 12
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 11
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000003974 aralkylamines Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 30
- 102000004877 Insulin Human genes 0.000 description 16
- 108090001061 Insulin Proteins 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229940125396 insulin Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000004283 biguanides Chemical class 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000003610 charcoal Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012803 melt mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 salt compound Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000004317 sodium nitrate Substances 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- SUYJXERPRICYRX-UHFFFAOYSA-N (3-bromophenyl)methanamine Chemical compound NCC1=CC=CC(Br)=C1 SUYJXERPRICYRX-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 2
- DXENBVSHQHBTBD-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NCC1=CC=C(Cl)C=C1 DXENBVSHQHBTBD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- KZNAUVKZACBZPF-UHFFFAOYSA-N (4-chlorophenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=C(Cl)C=C1 KZNAUVKZACBZPF-UHFFFAOYSA-N 0.000 description 1
- COWZNYTZVVEEKO-UHFFFAOYSA-N (4-methoxyphenyl)methylazanium;chloride Chemical compound Cl.COC1=CC=C(CN)C=C1 COWZNYTZVVEEKO-UHFFFAOYSA-N 0.000 description 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- KLULAEAPTZQZMV-UHFFFAOYSA-N 1-(diaminomethylidene)-2-[(4-methoxyphenyl)methyl]guanidine Chemical compound COC1=CC=C(CN=C(N)N=C(N)N)C=C1 KLULAEAPTZQZMV-UHFFFAOYSA-N 0.000 description 1
- RPYMNSQKHDXUSH-UHFFFAOYSA-N 1-(diaminomethylidene)-2-pentan-3-ylguanidine;hydrochloride Chemical compound Cl.CCC(CC)NC(=N)NC(N)=N RPYMNSQKHDXUSH-UHFFFAOYSA-N 0.000 description 1
- UDKGXKYEWBGQCG-UHFFFAOYSA-N 1-bromo-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Br)=C1 UDKGXKYEWBGQCG-UHFFFAOYSA-N 0.000 description 1
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 1
- AFKKTHZFBOANFY-UHFFFAOYSA-N 2-methylbutylazanium;chloride Chemical compound [Cl-].CCC(C)C[NH3+] AFKKTHZFBOANFY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PBOOZQFGWNZNQE-UHFFFAOYSA-N 3-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=C1 PBOOZQFGWNZNQE-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- RYIGNEOBDRVTHA-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2 RYIGNEOBDRVTHA-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 102000005237 Isophane Insulin Human genes 0.000 description 1
- 108010081368 Isophane Insulin Proteins 0.000 description 1
- CBSOFSBFHDQRLV-UHFFFAOYSA-N N-methylbenzylamine hydrochloride Chemical compound [Cl-].C[NH2+]CC1=CC=CC=C1 CBSOFSBFHDQRLV-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DALDFSUQXSXQBO-UHFFFAOYSA-N [N+](=O)(O)[O-].C(CCC)NC(=N)NC(=N)N Chemical compound [N+](=O)(O)[O-].C(CCC)NC(=N)NC(=N)N DALDFSUQXSXQBO-UHFFFAOYSA-N 0.000 description 1
- KKLWSPPIRBIEOV-UHFFFAOYSA-N [n'-(n'-butylcarbamimidoyl)carbamimidoyl]azanium;chloride Chemical compound Cl.CCCCN=C(N)N=C(N)N KKLWSPPIRBIEOV-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
- LEMUFSYUPGXXCM-JNEQYSBXSA-N caninsulin Chemical compound [Zn].C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3N=CN=C3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1C=NC=N1 LEMUFSYUPGXXCM-JNEQYSBXSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 239000004026 insulin derivative Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000006996 mental state Effects 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- FZFZFCIODKYFEV-UHFFFAOYSA-N pentan-1-amine;hydrochloride Chemical compound Cl.CCCCCN FZFZFCIODKYFEV-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- SNZAGZGEMYZBEO-UHFFFAOYSA-N pentan-3-ylazanium;chloride Chemical compound Cl.CCC(N)CC SNZAGZGEMYZBEO-UHFFFAOYSA-N 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B1/00—Constructions in general; Structures which are not restricted either to walls, e.g. partitions, or floors or ceilings or roofs
- E04B1/62—Insulation or other protection; Elements or use of specified material therefor
- E04B1/92—Protection against other undesired influences or dangers
- E04B1/94—Protection against other undesired influences or dangers against fire
- E04B1/941—Building elements specially adapted therefor
- E04B1/943—Building elements specially adapted therefor elongated
- E04B1/944—Building elements specially adapted therefor elongated covered with fire-proofing material
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Rod-Shaped Construction Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4843367 | 1967-10-25 | ||
| GB5443967 | 1967-11-30 | ||
| GB6468/68A GB1201820A (en) | 1967-10-25 | 1968-02-09 | Improvements in or relating to casings for joists, columns and other structural members |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127359B true NO127359B (de) | 1973-06-12 |
Family
ID=27254843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04205/68A NO127359B (de) | 1967-10-25 | 1968-10-24 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3590547A (de) |
| AT (1) | AT294389B (de) |
| BE (1) | BE722816A (de) |
| CH (1) | CH500358A (de) |
| DE (1) | DE1803478A1 (de) |
| FI (1) | FI47682C (de) |
| FR (1) | FR1588059A (de) |
| GB (1) | GB1201820A (de) |
| NL (1) | NL6814897A (de) |
| NO (1) | NO127359B (de) |
| SE (1) | SE341249B (de) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2207224B1 (de) * | 1972-11-20 | 1975-01-03 | Serpro | |
| US4084368A (en) * | 1976-01-23 | 1978-04-18 | Kenneth Morris Stilts | Apparatus for insulating purlins |
| US4279112A (en) * | 1979-01-19 | 1981-07-21 | Yves Bertrand | Method for improving the thermic insulation of a building with a rigid frame structure |
| DE3011392A1 (de) * | 1980-03-25 | 1981-10-08 | Odenwald Faserplattenwerk Gmbh, 8762 Amorbach | Bausatz mit klemmvorrichtung und leiste fuer einen verkleidungsaufbau |
| DE3022558A1 (de) * | 1980-06-16 | 1982-01-14 | Fitecpro AG, Glarus | Brandschutzkanal fuer traeger, stuetzen und aehnliche bauelemente |
| DE3812426A1 (de) * | 1988-04-14 | 1989-11-09 | Menzel Leuchten Gmbh & Co Kg | Saeule aus holz |
| US4904151A (en) * | 1988-07-07 | 1990-02-27 | Deere & Company | Loader lift arm structure |
| US4955173A (en) * | 1989-09-21 | 1990-09-11 | Czechowski John K | Structural steel corrosion protection by inert gas |
| US6003275A (en) * | 1990-02-14 | 1999-12-21 | Steelcase Development Inc. | Furniture system |
| US6170200B1 (en) | 1990-02-14 | 2001-01-09 | Steelcase Development Inc. | Furniture system |
| US6134844A (en) | 1990-02-14 | 2000-10-24 | Steelcase Inc. | Method and apparatus for displaying information |
| US5511348A (en) | 1990-02-14 | 1996-04-30 | Steelcase Inc. | Furniture system |
| US5568709A (en) * | 1995-07-28 | 1996-10-29 | Steckler; Richard D. | Simulated decorative architectural columns and method of making the same |
| CA2213831C (en) * | 1996-09-09 | 2001-12-04 | Finn A. Rasmussen | Modular pillar |
| CA2206830A1 (en) | 1997-05-15 | 1998-11-15 | Le Groupe Canam Manac Inc. | High rise steel column |
| US6308481B1 (en) * | 1999-02-19 | 2001-10-30 | Jack Goldberg | Cosmetic enhancement of overpass structure |
| AU2002300479B2 (en) * | 2000-01-12 | 2005-10-27 | Classic Columns Australia Pty Ltd | Architectural Column And Method And Apparatus For Production |
| AUPQ505600A0 (en) | 2000-01-12 | 2000-02-03 | Koszo, Nandor | Brick-work architectural pillar and method of production |
| US6242070B1 (en) * | 2000-02-09 | 2001-06-05 | Eagle Manufacturing Company | Energy absorbing column protector |
| GB2383346B (en) * | 2001-12-21 | 2005-08-03 | Glazing System Profiles Ltd | Structural building elements |
| US20040040245A1 (en) * | 2002-04-11 | 2004-03-04 | Sinclair Robert F. | Building block and system for manufacture |
| US20050056822A1 (en) * | 2003-09-12 | 2005-03-17 | Linford Paul M. | Apparatus and method for reinforcing a vinyl beam |
| US7721496B2 (en) | 2004-08-02 | 2010-05-25 | Tac Technologies, Llc | Composite decking material and methods associated with the same |
| US8065848B2 (en) * | 2007-09-18 | 2011-11-29 | Tac Technologies, Llc | Structural member |
| US8266856B2 (en) | 2004-08-02 | 2012-09-18 | Tac Technologies, Llc | Reinforced structural member and frame structures |
| US7213379B2 (en) | 2004-08-02 | 2007-05-08 | Tac Technologies, Llc | Engineered structural members and methods for constructing same |
| US7930866B2 (en) | 2004-08-02 | 2011-04-26 | Tac Technologies, Llc | Engineered structural members and methods for constructing same |
| US20070028541A1 (en) * | 2005-08-02 | 2007-02-08 | Mark Joseph Pasek | Prefabricated shell concrete structural components |
| KR100797194B1 (ko) * | 2007-04-26 | 2008-01-29 | (주)엠씨에스공법 | 콘크리트 복합 기둥 및 이를 이용한 건축물 시공방법 |
| WO2010017305A1 (en) * | 2008-08-05 | 2010-02-11 | Atlas Bolt & Screw Company | Fastener blanket |
| JP4245657B1 (ja) * | 2008-10-24 | 2009-03-25 | 朝日エンヂニヤリング株式会社 | 橋脚とコンクリート桁の剛結合構造 |
| KR101086853B1 (ko) * | 2011-09-02 | 2011-11-25 | 계명대학교 산학협력단 | 건물기둥 구조물 내진 보강 구조체 |
| US9133625B2 (en) * | 2013-12-18 | 2015-09-15 | Moulure Alexandria Moulding | Sheathing element for covering preexisting physical structures |
| DE102014001893A1 (de) * | 2014-02-12 | 2015-08-13 | Rwe Deutschland Ag | Aerodynamische Verkleidung an Fachwerkstrukturen sowie Verfahren zur Standfestigkeitserhöhung von Fachwerkstrukturen |
| WO2016123623A1 (en) * | 2015-01-31 | 2016-08-04 | Sentry Protection Products | Column protector and column protection system |
| WO2022155759A1 (zh) * | 2021-01-20 | 2022-07-28 | 洪崇展 | 模板件以及模板组合 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US219120A (en) * | 1879-09-02 | Improvement in fire-proof chimneys | ||
| US338512A (en) * | 1886-03-23 | Fire-proof post and column | ||
| GB105191A (en) * | 1916-08-28 | 1917-04-05 | Herbert Stuart Smith | Improvements in the Construction of Wooden Batch Rollers employed in Textile and other Machines. |
| FR674353A (fr) * | 1928-07-13 | 1930-01-28 | Système de transformation progressive des poteaux en bois ou métalliques en des pylônes en béton et nouveau produit industriel en résultant | |
| US2074463A (en) * | 1933-02-08 | 1937-03-23 | American Cyanamid & Chem Corp | Fireproofing slab |
| US2016382A (en) * | 1933-03-10 | 1935-10-08 | Owens Illinois Glass Co | Furnace tank construction |
| GB550434A (en) * | 1941-09-02 | 1943-01-07 | Dionisio David Capeila | Improvements in encasements or coverings for metal joists, girders and the like |
| US2664739A (en) * | 1948-01-02 | 1954-01-05 | John P Marcy | Tile covered, fireproofed structural element |
| US2580174A (en) * | 1948-12-31 | 1951-12-25 | Peoples First Nat Bank & Trust | Connection for precast concrete girders and beams |
| LU49852A1 (de) * | 1965-11-16 | 1966-01-17 |
-
1968
- 1968-02-09 GB GB6468/68A patent/GB1201820A/en not_active Expired
- 1968-05-28 DE DE19681803478 patent/DE1803478A1/de active Pending
- 1968-10-17 NL NL6814897A patent/NL6814897A/xx unknown
- 1968-10-21 US US769234A patent/US3590547A/en not_active Expired - Lifetime
- 1968-10-22 CH CH1602668A patent/CH500358A/fr not_active IP Right Cessation
- 1968-10-24 BE BE722816D patent/BE722816A/xx unknown
- 1968-10-24 AT AT1037168A patent/AT294389B/de active
- 1968-10-24 NO NO04205/68A patent/NO127359B/no unknown
- 1968-10-25 SE SE14452/68A patent/SE341249B/xx unknown
- 1968-10-25 FR FR1588059D patent/FR1588059A/fr not_active Expired
- 1968-10-25 FI FI683036A patent/FI47682C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1201820A (en) | 1970-08-12 |
| AT294389B (de) | 1971-11-25 |
| FR1588059A (de) | 1970-04-03 |
| NL6814897A (de) | 1969-04-29 |
| SE341249B (de) | 1971-12-20 |
| US3590547A (en) | 1971-07-06 |
| FI47682B (de) | 1973-10-31 |
| BE722816A (de) | 1969-04-01 |
| FI47682C (fi) | 1974-02-11 |
| CH500358A (fr) | 1970-12-15 |
| DE1803478A1 (de) | 1969-05-22 |
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