SU1450742A3 - Способ получени производных бензоатных эфиров 3-оксиморфинана - Google Patents

Способ получени производных бензоатных эфиров 3-оксиморфинана Download PDF

Info

Publication number: SU1450742A3
Authority: SU; USSR - Soviet Union
Prior art keywords: dogs; bioavailability; base; oxymorphinan; cyclobutylmethyl
Prior art date: 1984-07-05

Application number

SU853920678A

Other languages

English (en)

Russian (ru)

Inventor

Габриель Шами Элай

Original Assignee

Е.И.Дюпон Де Немур Энд Компани (Фирма)

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.)

1984-07-05

Filing date

1985-07-04

Publication date

1989-01-07

1985-07-04 Application filed by Е.И.Дюпон Де Немур Энд Компани (Фирма) filed Critical Е.И.Дюпон Де Немур Энд Компани (Фирма)

1989-01-07 Application granted granted Critical

1989-01-07 Publication of SU1450742A3 publication Critical patent/SU1450742A3/ru

Links

-1 derivatives of benzoate ethers Chemical class 0.000 title claims abstract 4
238000000034 method Methods 0.000 title claims description 12
241000282472 Canis lupus familiaris Species 0.000 claims description 10
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 9
229960000805 nalbuphine Drugs 0.000 claims description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
241000282693 Cercopithecidae Species 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
229960005181 morphine Drugs 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
239000000010 aprotic solvent Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
IYNWSQDZXMGGGI-NUEKZKHPSA-N 3-hydroxymorphinan Chemical class C1CCC[C@H]2[C@H]3CC4=CC=C(O)C=C4[C@]21CCN3 IYNWSQDZXMGGGI-NUEKZKHPSA-N 0.000 abstract description 3
229940035676 analgesics Drugs 0.000 abstract description 2
239000000730 antalgic agent Substances 0.000 abstract description 2
239000003887 narcotic antagonist Substances 0.000 abstract 1
229940002612 prodrug Drugs 0.000 abstract 1
239000000651 prodrug Substances 0.000 abstract 1
239000003814 drug Substances 0.000 description 18
229940079593 drug Drugs 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000000556 agonist Substances 0.000 description 2
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 description 2
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 2
229960004127 naloxone Drugs 0.000 description 2
DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 description 2
229960003086 naltrexone Drugs 0.000 description 2
238000009101 premedication Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 1
229960001736 buprenorphine Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/28—Morphinans
- 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:
- C07D489/02—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 oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU853920678A 1984-07-05 1985-07-04 Способ получени производных бензоатных эфиров 3-оксиморфинана SU1450742A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62792384A	1984-07-05	1984-07-05
US06/733,464 US4668685A (en)	1984-07-05	1985-05-14	Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans, which are analgesics or narcotic antagonists

Publications (1)

Publication Number	Publication Date
SU1450742A3 true SU1450742A3 (ru)	1989-01-07

Family

ID=27090564

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU853920678A SU1450742A3 (ru)	1984-07-05	1985-07-04	Способ получени производных бензоатных эфиров 3-оксиморфинана
SU874202841A SU1508960A3 (ru)	1984-07-05	1987-07-03	Способ получени производных бензоатных эфиров 3-оксиморфинанов

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU874202841A SU1508960A3 (ru)	1984-07-05	1987-07-03	Способ получени производных бензоатных эфиров 3-оксиморфинанов

Country Status (18)

Country	Link
US (1)	US4668685A (2)
EP (1)	EP0170090B1 (2)
AU (1)	AU578391B2 (2)
CA (1)	CA1301150C (2)
DE (1)	DE3573251D1 (2)
DK (1)	DK160501C (2)
ES (1)	ES8704443A1 (2)
FI (1)	FI83215C (2)
GR (1)	GR851653B (2)
HK (1)	HK39790A (2)
HU (1)	HU193995B (2)
IE (1)	IE58136B1 (2)
IL (1)	IL75721A (2)
MX (1)	MX160445A (2)
NO (1)	NO171209C (2)
NZ (1)	NZ212641A (2)
PT (1)	PT80773B (2)
SU (2)	SU1450742A3 (2)

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JPS59184163A (ja) *	1983-04-02	1984-10-19	Res Inst For Prod Dev	３−ベンゾイルチオ−１７−メチルモルヒナン
JPS59184182A (ja) *	1983-04-02	1984-10-19	Res Inst For Prod Dev	３−ベンゾイルチオ−４、５α−エポキシ−７α−〔１（Ｒ）−ヒドロキシ−１−メチルベンチル〕−６−メトキシ−１７−メチル−６、１４−エンド−エタノモルヒナン
JPS59184183A (ja) *	1983-04-02	1984-10-19	Res Inst For Prod Dev	３−ベンゾイルチオ−４、５α−エポキシ−７α−〔１（Ｒ）−ヒドロキシ−１−メチルブチル〕−６−メトキシ−１７−メチル−６、１４−エンド−エテノモルヒナン
JPS59186987A (ja) *	1983-04-06	1984-10-23	Res Inst For Prod Dev	３−ベンゾイルチオ−４、５α−エポキシ−７α−〔１（Ｒ）−ヒドロキシ−１−メチルブチル〕−６−メトキシ−１７−メチル−６、１４−エンド−エテノモルヒナン

1985
- 1985-05-14 US US06/733,464 patent/US4668685A/en not_active Expired - Lifetime
- 1985-06-27 CA CA000485661A patent/CA1301150C/en not_active Expired - Lifetime
- 1985-07-03 DE DE8585108258T patent/DE3573251D1/de not_active Expired
- 1985-07-03 EP EP85108258A patent/EP0170090B1/en not_active Expired
- 1985-07-03 AU AU44516/85A patent/AU578391B2/en not_active Ceased
- 1985-07-04 HU HU852607A patent/HU193995B/hu not_active IP Right Cessation
- 1985-07-04 SU SU853920678A patent/SU1450742A3/ru active
- 1985-07-04 DK DK306885A patent/DK160501C/da not_active IP Right Cessation
- 1985-07-04 NZ NZ212641A patent/NZ212641A/xx unknown
- 1985-07-04 GR GR851653A patent/GR851653B/el unknown
- 1985-07-04 ES ES544852A patent/ES8704443A1/es not_active Expired
- 1985-07-04 IE IE168385A patent/IE58136B1/en not_active IP Right Cessation
- 1985-07-04 NO NO852699A patent/NO171209C/no unknown
- 1985-07-04 PT PT80773A patent/PT80773B/pt not_active IP Right Cessation
- 1985-07-04 IL IL75721A patent/IL75721A/xx not_active IP Right Cessation
- 1985-07-04 FI FI852659A patent/FI83215C/fi not_active IP Right Cessation
- 1985-07-05 MX MX6144A patent/MX160445A/es unknown
1987
- 1987-07-03 SU SU874202841A patent/SU1508960A3/ru active
1990
- 1990-05-24 HK HK397/90A patent/HK39790A/xx unknown

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* Cited by examiner, † Cited by third party
Title
Патент US № 3254088, - . .кл. 260-285, 1966. Патент DE № 2323192, кл. С 07 D 489/02, 1973. *

Also Published As

Publication number	Publication date
DK306885D0 (da)	1985-07-04
IE58136B1 (en)	1993-07-14
NO852699L (no)	1986-01-06
DK306885A (da)	1986-01-06
FI83215C (fi)	1991-06-10
SU1508960A3 (ru)	1989-09-15
FI83215B (fi)	1991-02-28
MX160445A (es)	1990-03-02
NZ212641A (en)	1988-10-28
AU4451685A (en)	1986-01-09
DE3573251D1 (en)	1989-11-02
FI852659A0 (fi)	1985-07-04
IE851683L (en)	1986-01-05
FI852659L (fi)	1986-01-06
PT80773B (pt)	1987-10-20
PT80773A (en)	1985-08-01
DK160501C (da)	1991-08-26
CA1301150C (en)	1992-05-19
EP0170090B1 (en)	1989-09-27
NO171209C (no)	1993-02-10
ES544852A0 (es)	1987-04-01
DK160501B (da)	1991-03-18
NO171209B (no)	1992-11-02
HUT40132A (en)	1986-11-28
ES8704443A1 (es)	1987-04-01
US4668685A (en)	1987-05-26
AU578391B2 (en)	1988-10-20
IL75721A (en)	1990-04-29
GR851653B (2)	1985-11-26
EP0170090A1 (en)	1986-02-05
HU193995B (en)	1987-12-28
HK39790A (en)	1990-06-01
IL75721A0 (en)	1985-11-29

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