DE102634C - - Google Patents

Info

Publication number

DE102634C

DE102634C DE1898102634D DE102634DD DE102634C DE 102634 C DE102634 C DE 102634C DE 1898102634 D DE1898102634 D DE 1898102634D DE 102634D D DE102634D D DE 102634DD DE 102634 C DE102634 C DE 102634C

Authority

DE

Germany

Prior art keywords

morphine

alkali

codeine

code

methylmorphine

Prior art date

1898-05-22

Legal status (The legal status 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 status listed.)

Expired

Links

• Espacenet
• Global Dossier
• DPMA
• Discuss

• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 31
• 229960005181 morphine Drugs 0.000 claims description 16
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 13
• 229960004126 codeine Drugs 0.000 claims description 8
• 239000003513 alkali Substances 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
• 230000001476 alcoholic effect Effects 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 230000007935 neutral effect Effects 0.000 claims description 2
• OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 claims 1
• OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 claims 1
• 229960004578 ethylmorphine Drugs 0.000 claims 1
• 238000000034 method Methods 0.000 description 8
• OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 4
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 239000000243 solution Substances 0.000 description 3
• -1 sulfuric acid ester Chemical class 0.000 description 3
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
• 239000012670 alkaline solution Substances 0.000 description 2
• 150000005215 alkyl ethers Chemical class 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• ZENNIHDHUIWZRA-SEJAZBPASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC ZENNIHDHUIWZRA-SEJAZBPASA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical class CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• CAUBWLYZCDDYEF-UHFFFAOYSA-N N-Nitroso-N-methylurethane Chemical compound CCOC(=O)N(C)N=O CAUBWLYZCDDYEF-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 238000001311 chemical methods and process Methods 0.000 description 1
• 238000010411 cooking Methods 0.000 description 1
• DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
• 229940008406 diethyl sulfate Drugs 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000012022 methylating agents‎ Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 238000010792 warming Methods 0.000 description 1