DD154541A5 - Verfahren zur herstellung von amidverbindungen - Google Patents

Verfahren zur herstellung von amidverbindungen Download PDF

Info

Publication number: DD154541A5
Authority: DD; German Democratic Republic
Prior art keywords: amide; compounds; item; carbon atoms; boron
Prior art date: 1979-08-09

Application number

DD80223221A

Other languages

German (de)

English (en)

Inventor

Dennis I Malfer

Donald F Loncrini

Original Assignee

Mallinckrodt Inc

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.)

1979-08-09

Filing date

1980-09-08

Publication date

1982-03-31

1980-09-08 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1982-03-31 Publication of DD154541A5 publication Critical patent/DD154541A5/de

Links

150000001875 compounds Chemical class 0.000 title abstract description 22
238000004519 manufacturing process Methods 0.000 title abstract description 3
150000001408 amides Chemical class 0.000 claims abstract description 37
238000000034 method Methods 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
239000012649 demethylating agent Substances 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 12
-1 amide compounds Chemical class 0.000 claims abstract description 11
150000001639 boron compounds Chemical class 0.000 claims abstract description 8
239000004215 Carbon black (E152) Substances 0.000 claims abstract 4
229930195733 hydrocarbon Natural products 0.000 claims abstract 4
230000001335 demethylating effect Effects 0.000 claims abstract 3
230000017858 demethylation Effects 0.000 claims description 8
238000010520 demethylation reaction Methods 0.000 claims description 8
239000012429 reaction media Substances 0.000 claims description 7
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 5
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 37
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 abstract description 4
239000003887 narcotic antagonist Substances 0.000 abstract description 3
229940035676 analgesics Drugs 0.000 abstract 2
239000000730 antalgic agent Substances 0.000 abstract 2
125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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 description 14
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229960000805 nalbuphine Drugs 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
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 5
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 5
229960002085 oxycodone Drugs 0.000 description 5
229960005118 oxymorphone Drugs 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
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 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000010189 synthetic method Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
238000003776 cleavage reaction Methods 0.000 description 2
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 2
ZIQIQOUPRHPOIT-UHFFFAOYSA-N cyclobutylazanide Chemical compound [NH-]C1CCC1 ZIQIQOUPRHPOIT-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
238000003786 synthesis reaction Methods 0.000 description 2
VPMMJSPGZSFEAH-UHFFFAOYSA-N 2,4-diaminophenol;hydrochloride Chemical compound [Cl-].NC1=CC=C(O)C([NH3+])=C1 VPMMJSPGZSFEAH-UHFFFAOYSA-N 0.000 description 1
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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
206010038678 Respiratory depression Diseases 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
229940124326 anaesthetic agent Drugs 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000013101 initial test Methods 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
PFBSOANQDDTNGJ-YNHQPCIGSA-N morphinone Chemical compound O([C@H]1C(C=C[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O PFBSOANQDDTNGJ-YNHQPCIGSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000012360 testing method Methods 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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD80223221A 1979-08-09 1980-09-08 Verfahren zur herstellung von amidverbindungen DD154541A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6527579A	1979-08-09	1979-08-09

Publications (1)

Publication Number	Publication Date
DD154541A5 true DD154541A5 (de)	1982-03-31

Family

ID=22061564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80223221A DD154541A5 (de)	1979-08-09	1980-09-08	Verfahren zur herstellung von amidverbindungen

Country Status (16)

Country	Link
JP (1)	JPS56501010A (fr)
AU (1)	AU6116580A (fr)
BE (1)	BE884671A (fr)
DD (1)	DD154541A5 (fr)
DK (1)	DK151781A (fr)
ES (1)	ES8104296A1 (fr)
FI (1)	FI802479A7 (fr)
FR (1)	FR2465735A1 (fr)
GB (1)	GB2066256A (fr)
IL (1)	IL60783A0 (fr)
IT (1)	IT8068267A0 (fr)
NL (1)	NL8020319A (fr)
NO (1)	NO802139L (fr)
PL (1)	PL226162A1 (fr)
SE (1)	SE8102214L (fr)
WO (1)	WO1981000409A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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 (fr) *	1989-10-16	1998-06-30	Kenner C. Rice	Synthese totale d'enantiomeres de la northebaine, normorphine, noroxymorphone et de leurs derives par des intermediaires n-nor

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3249616A (en) *		1966-05-03		Ix-dfflydroxy-g-oxo-n-phenethylmor- phinan (cis) and production thereof
CA913077A (en) *		1972-10-24	J. Pachter Irwin	Process of preparing n-substituted 14-hydroxydihydronormorphines
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 (fr) *	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 AU AU61165/80A patent/AU6116580A/en not_active Abandoned
- 1980-08-07 IL IL60783A patent/IL60783A0/xx unknown
- 1980-08-07 NL NL8020319A patent/NL8020319A/nl not_active Application Discontinuation
- 1980-08-07 WO PCT/US1980/000998 patent/WO1981000409A1/fr not_active Ceased
- 1980-08-07 GB GB8107295A patent/GB2066256A/en not_active Withdrawn
- 1980-08-07 JP JP50198480A patent/JPS56501010A/ja active Pending
- 1980-08-07 FI FI802479A patent/FI802479A7/fi not_active Application Discontinuation
- 1980-08-07 BE BE0/201677A patent/BE884671A/fr unknown
- 1980-08-07 IT IT8068267A patent/IT8068267A0/it unknown
- 1980-08-08 FR FR8017530A patent/FR2465735A1/fr not_active Withdrawn
- 1980-08-08 ES ES494122A patent/ES8104296A1/es not_active Expired
- 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
ES494122A0 (es)	1981-04-16
SE8102214L (sv)	1981-04-07
IT8068267A0 (it)	1980-08-07
WO1981000409A1 (fr)	1981-02-19
DK151781A (da)	1981-04-03
NO802139L (no)	1981-02-10
FI802479A7 (fi)	1981-01-01
JPS56501010A (fr)	1981-07-23
ES8104296A1 (es)	1981-04-16
GB2066256A (en)	1981-07-08
BE884671A (fr)	1980-12-01
FR2465735A1 (fr)	1981-03-27
IL60783A0 (en)	1980-10-26
NL8020319A (nl)	1981-07-01
AU6116580A (en)	1981-02-12
PL226162A1 (fr)	1981-04-24

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