NL8020319A - Tussenprodukten voor het bereiden van morfinederivaten. - Google Patents
Tussenprodukten voor het bereiden van morfinederivaten. Download PDFInfo
- Publication number
- NL8020319A NL8020319A NL8020319A NL8020319A NL8020319A NL 8020319 A NL8020319 A NL 8020319A NL 8020319 A NL8020319 A NL 8020319A NL 8020319 A NL8020319 A NL 8020319A NL 8020319 A NL8020319 A NL 8020319A
- Authority
- NL
- Netherlands
- Prior art keywords
- amide
- boron
- compounds
- carbon atoms
- nalbuphine
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title description 11
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class 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 title description 6
- 150000001408 amides Chemical class 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims description 16
- 239000012649 demethylating agent Substances 0.000 claims description 13
- 229960000805 nalbuphine Drugs 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 6
- -1 amide compounds Chemical class 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001639 boron compounds Chemical class 0.000 claims description 4
- 230000017858 demethylation Effects 0.000 claims description 4
- 238000010520 demethylation reaction Methods 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 230000001335 demethylating effect Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229960002085 oxycodone Drugs 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RIKMCJUNPCRFMW-ISWURRPUSA-N Noroxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4 RIKMCJUNPCRFMW-ISWURRPUSA-N 0.000 description 3
- HLMSIZPQBSYUNL-IPOQPSJVSA-N Noroxymorphone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4 HLMSIZPQBSYUNL-IPOQPSJVSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229960005118 oxymorphone Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- YPSXFMHXRZAGTG-UHFFFAOYSA-N 4-methoxy-2-[2-(5-methoxy-2-nitrosophenyl)ethyl]-1-nitrosobenzene Chemical compound COC1=CC=C(N=O)C(CCC=2C(=CC=C(OC)C=2)N=O)=C1 YPSXFMHXRZAGTG-UHFFFAOYSA-N 0.000 description 1
- 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000009937 cyclo 3 Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- ZIQIQOUPRHPOIT-UHFFFAOYSA-N cyclobutylazanide Chemical compound [NH-]C1CCC1 ZIQIQOUPRHPOIT-UHFFFAOYSA-N 0.000 description 1
- 238000005115 demineralization Methods 0.000 description 1
- 230000002328 demineralizing effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6527579A | 1979-08-09 | 1979-08-09 | |
| US6527579 | 1979-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8020319A true NL8020319A (nl) | 1981-07-01 |
Family
ID=22061564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8020319A NL8020319A (nl) | 1979-08-09 | 1980-08-07 | Tussenprodukten voor het bereiden van morfinederivaten. |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS56501010A (online.php) |
| AU (1) | AU6116580A (online.php) |
| BE (1) | BE884671A (online.php) |
| DD (1) | DD154541A5 (online.php) |
| DK (1) | DK151781A (online.php) |
| ES (1) | ES494122A0 (online.php) |
| FI (1) | FI802479A7 (online.php) |
| FR (1) | FR2465735A1 (online.php) |
| GB (1) | GB2066256A (online.php) |
| IL (1) | IL60783A0 (online.php) |
| IT (1) | IT8068267A0 (online.php) |
| NL (1) | NL8020319A (online.php) |
| NO (1) | NO802139L (online.php) |
| PL (1) | PL226162A1 (online.php) |
| SE (1) | SE8102214L (online.php) |
| WO (1) | WO1981000409A1 (online.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795813A (en) * | 1981-08-17 | 1989-01-03 | The Florida Board Of Regents On Behalf Of The Florida State University | Synthesis of derivatives of codeine and other 3-O-alkylmorphines |
| US5668285A (en) * | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| CA2067200C (en) * | 1989-10-16 | 1998-06-30 | Kenner C. Rice | Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA913077A (en) * | 1972-10-24 | J. Pachter Irwin | Process of preparing n-substituted 14-hydroxydihydronormorphines | |
| US3249616A (en) * | 1966-05-03 | Ix-dfflydroxy-g-oxo-n-phenethylmor- phinan (cis) and production thereof | ||
| US2772270A (en) * | 1954-10-21 | 1956-11-27 | M J Lewenstein | 14-hydroxymorphinone and 8, 14-dihydroxydihydromorphinone |
| US2806033A (en) * | 1955-08-03 | 1957-09-10 | Lewenstein | Morphine derivative |
| BE638369A (online.php) * | 1962-10-10 | |||
| US3332950A (en) * | 1963-03-23 | 1967-07-25 | Endo Lab | 14-hydroxydihydronormorphinone derivatives |
| NL7106612A (en) * | 1971-05-13 | 1972-11-15 | N-cycloalkylalkyl-14-hydroxy-dihydronormorphines - - by o-demethylation of 14-methoxy cpds | |
| US3775414A (en) * | 1972-05-10 | 1973-11-27 | Bristol Myers Co | Process for the preparation of 14-hydroxymorphinan derivatives |
| US4161597A (en) * | 1976-12-20 | 1979-07-17 | Research Corporation | N-alkyl-14-hydroxymorphinans and derivatives |
-
1980
- 1980-07-16 NO NO802139A patent/NO802139L/no unknown
- 1980-08-07 FI FI802479A patent/FI802479A7/fi not_active Application Discontinuation
- 1980-08-07 WO PCT/US1980/000998 patent/WO1981000409A1/en not_active Ceased
- 1980-08-07 BE BE0/201677A patent/BE884671A/fr unknown
- 1980-08-07 IT IT8068267A patent/IT8068267A0/it unknown
- 1980-08-07 GB GB8107295A patent/GB2066256A/en not_active Withdrawn
- 1980-08-07 NL NL8020319A patent/NL8020319A/nl not_active Application Discontinuation
- 1980-08-07 AU AU61165/80A patent/AU6116580A/en not_active Abandoned
- 1980-08-07 JP JP50198480A patent/JPS56501010A/ja active Pending
- 1980-08-07 IL IL60783A patent/IL60783A0/xx unknown
- 1980-08-08 ES ES494122A patent/ES494122A0/es active Granted
- 1980-08-08 FR FR8017530A patent/FR2465735A1/fr not_active Withdrawn
- 1980-08-09 PL PL22616280A patent/PL226162A1/xx unknown
- 1980-09-08 DD DD80223221A patent/DD154541A5/de unknown
-
1981
- 1981-04-03 DK DK151781A patent/DK151781A/da not_active Application Discontinuation
- 1981-04-07 SE SE8102214A patent/SE8102214L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56501010A (online.php) | 1981-07-23 |
| GB2066256A (en) | 1981-07-08 |
| BE884671A (fr) | 1980-12-01 |
| ES8104296A1 (es) | 1981-04-16 |
| WO1981000409A1 (en) | 1981-02-19 |
| PL226162A1 (online.php) | 1981-04-24 |
| AU6116580A (en) | 1981-02-12 |
| ES494122A0 (es) | 1981-04-16 |
| FR2465735A1 (fr) | 1981-03-27 |
| IT8068267A0 (it) | 1980-08-07 |
| DD154541A5 (de) | 1982-03-31 |
| DK151781A (da) | 1981-04-03 |
| SE8102214L (sv) | 1981-04-07 |
| FI802479A7 (fi) | 1981-01-01 |
| IL60783A0 (en) | 1980-10-26 |
| NO802139L (no) | 1981-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |