CH389607A - Verfahren zur Herstellung von neuen Tropasäureestern - Google Patents

Verfahren zur Herstellung von neuen Tropasäureestern

Info

Publication number: CH389607A
Authority: CH; Switzerland
Prior art keywords: sep; water; solution; phenyl; acid
Prior art date: 1959-03-16

Application number

CH239760A

Other languages

German (de)

English (en)

Inventor

Vecchi Alberto

Melone Gaetano

Maffii Giulio

Testa Emilio

Original Assignee

Lepetit Spa

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.)

1959-03-16

Filing date

1960-03-03

Publication date

1965-03-31

1959-03-16 Priority claimed from GB9023/59A external-priority patent/GB874015A/en

1960-03-03 Application filed by Lepetit Spa filed Critical Lepetit Spa

1965-03-31 Publication of CH389607A publication Critical patent/CH389607A/de

Links

VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical class C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 13
XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 claims description 9
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 claims description 9
QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 6
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 claims description 6
239000002244 precipitate Substances 0.000 claims description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
239000003799 water insoluble solvent Substances 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002253 acid Substances 0.000 description 4
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229930003347 Atropine Natural products 0.000 description 3
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
229960000396 atropine Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
-1 tropine ester Chemical class 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229960005096 methylatropine Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
RCYPBSKFQORSRJ-UHFFFAOYSA-N (3-chloro-3-oxopropyl) acetate Chemical compound CC(=O)OCCC(Cl)=O RCYPBSKFQORSRJ-UHFFFAOYSA-N 0.000 description 1
ISSYFABJJSOCQG-UHFFFAOYSA-N 3-hydroxy-2-methyl-2-phenylpropanoic acid Chemical compound OCC(C)(C(O)=O)C1=CC=CC=C1 ISSYFABJJSOCQG-UHFFFAOYSA-N 0.000 description 1
CBSQLIKPLOWPGA-UHFFFAOYSA-N 3-hydroxy-2-phenylbutanoic acid Chemical compound CC(O)C(C(O)=O)C1=CC=CC=C1 CBSQLIKPLOWPGA-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH239760A 1959-03-16 1960-03-03 Verfahren zur Herstellung von neuen Tropasäureestern CH389607A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9023/59A GB874015A (en)	1959-03-16	1959-03-16	Tropine esters
GB3241759		1959-09-23

Publications (1)

Publication Number	Publication Date
CH389607A true CH389607A (de)	1965-03-31

Family

ID=26242588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH239760A CH389607A (de)	1959-03-16	1960-03-03	Verfahren zur Herstellung von neuen Tropasäureestern

Country Status (4)

Country	Link
BE (1)	BE588576A (fr)
CH (1)	CH389607A (fr)
DE (1)	DE1174324B (fr)
ES (1)	ES256310A1 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT198771B (de) *	1956-03-09	1958-07-25	Boehringer Sohn Ingelheim	Verfahren zur Herstellung von neuen Estern und deren Salzen

1960
- 1960-03-03 CH CH239760A patent/CH389607A/de unknown
- 1960-03-07 ES ES0256310A patent/ES256310A1/es not_active Expired
- 1960-03-11 BE BE588576A patent/BE588576A/fr unknown
- 1960-03-15 DE DEL35614A patent/DE1174324B/de active Pending

Also Published As

Publication number	Publication date
BE588576A (fr)	1960-07-01
DE1174324B (de)	1964-07-23
ES256310A1 (es)	1960-08-16

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DE2362687C3 (de)	1982-01-14	Verfahren zur Gewinnung der optischen Isomeren des Penicillamins
DE3906460C1 (fr)	1990-11-15
DE2258088A1 (de)	1974-04-18	Optisch aktive isoindolinderivate und verfahren zu ihrer herstellung
DE1274132B (de)	1968-08-01	Verfahren zur Herstellung von L-(í¬)-ª-(3, 4-Dihydroxyphenyl)-ª-methyl-alanin
AT224119B (de)	1962-11-12	Verfahren zur Isomerisierung von basisch substituierten tricyclischen Verbindungen
DE1568253C (de)	1973-02-22	N substituierte 1,2 Diphenyl 2 acyloxy 3 amino methyl butene
DE1209566B (de)	1966-01-27	Verfahren zur Herstellung von Gemischen von substituierten Glykolsaeure-pyrrolidyl-(2)-methylestern und substituierten Glykolsaeure-piperidyl-(3)-estern und deren Salzen
AT261592B (de)	1968-05-10	Verfahren zur Herstellung L-(-)-α-Methyl-β-(3,4-dihydroxyphenyl)-alanin
AT227266B (de)	1963-05-10	Verfahren zur Herstellung von neuen Phenothiazinderivaten, sowie von deren Säureadditionssalzen und quartären Salzen
DE681867C (de)	1939-10-03	Verfahren zur Herstellung monohalogenierter, ungesaettigter, einen Sterinkern enthaltender Ketone
AT203004B (de)	1959-04-25	Verfahren zur Herstellung von neuen Estern des Piperidyl-(2)-phenylcarbinols und von deren Salzen
DE710539C (de)	1941-09-16	Verfahren zur Herstellung eines Kondensationsproduktes
AT237589B (de)	1964-12-28	Verfahren zur Herstellung von basisch substituierten Dibenzoderivaten und deren Säureadditionssalzen oder quaternären Verbindungen
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