CS225849B2 - The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole - Google Patents

The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole Download PDF

Info

Publication number: CS225849B2
Authority: CS; Czechoslovakia
Prior art keywords: carbazole; pharmaceutically acceptable; cis; propyl; acid
Prior art date: 1978-11-01

Application number

CS7955482A

Other languages

Czech (cs)

English (en)

Inventor

Morton Harfenist

Charles T Joyner

Original Assignee

Wellcome Found

Process For Preparing 9 3 3

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.)

1978-11-01

Filing date

1979-10-31

Publication date

1984-02-13

1979-10-31 Application filed by Wellcome Found, Process For Preparing 9 3 3 filed Critical Wellcome Found

1984-02-13 Publication of CS225849B2 publication Critical patent/CS225849B2/cs

Links

UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title description 76
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
150000003839 salts Chemical class 0.000 claims description 37
239000012453 solvate Substances 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
GUDVQJXODNJRIJ-CALCHBBNSA-N 9-[3-[(3S,5R)-3,5-dimethyl-1-piperazinyl]propyl]carbazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1CCCN1C2=CC=CC=C2C2=CC=CC=C21 GUDVQJXODNJRIJ-CALCHBBNSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000000203 mixture Substances 0.000 description 14
-1 aliphatic hydrocarbon radical Chemical class 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
238000011282 treatment Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
208000028017 Psychotic disease Diseases 0.000 description 8
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239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
230000000561 anti-psychotic effect Effects 0.000 description 5
239000003814 drug Substances 0.000 description 5
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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238000001914 filtration Methods 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
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BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
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OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
208000012761 aggressive behavior Diseases 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
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VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
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239000002775 capsule Substances 0.000 description 2
150000001716 carbazoles Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 description 1
CLPZHEDSMNQBPP-KNVOCYPGSA-N (3s,5r)-1,3,5-trimethylpiperazine Chemical compound C[C@H]1CN(C)C[C@@H](C)N1 CLPZHEDSMNQBPP-KNVOCYPGSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
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SYOCXNBBHXIBDZ-UHFFFAOYSA-N CN(C=O)C.C1=CC=CC=2C3=CC=CC=C3NC12 Chemical compound CN(C=O)C.C1=CC=CC=2C3=CC=CC=C3NC12 SYOCXNBBHXIBDZ-UHFFFAOYSA-N 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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RHQKKJPJCHGKQO-UHFFFAOYSA-N [Cu+2].[O-][Cr]([O-])=O Chemical compound [Cu+2].[O-][Cr]([O-])=O RHQKKJPJCHGKQO-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
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ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
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239000012971 dimethylpiperazine Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

CS7955482A 1978-11-01 1979-10-31 The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole CS225849B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7842845		1978-11-01

Publications (1)

Publication Number	Publication Date
CS225849B2 true CS225849B2 (en)	1984-02-13

Family

ID=10500744

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS7955482A CS225849B2 (en)	1978-11-01	1979-10-31	The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole
CS797407A CS225817B2 (en)	1978-11-01	1979-10-31	The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS797407A CS225817B2 (en)	1978-11-01	1979-10-31	The production of the 9-/3-/3,5-cis/dimenhylpiperazine/propyl/carbazole

Country Status (8)

Country	Link
JP (1)	JPS5564585A (pl)
KR (1)	KR830001276A (pl)
AT (1)	AT377760B (pl)
CS (2)	CS225849B2 (pl)
HU (1)	HU184705B (pl)
PL (2)	PL128831B1 (pl)
SU (3)	SU1014469A3 (pl)
ZA (1)	ZA787352B (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4400383A (en)	1981-12-11	1983-08-23	Burroughs Wellcome Co.	Treatment of anxiety
EP1094063A1 (en)	1999-10-18	2001-04-25	Applied Research Systems ARS Holding N.V.	9-(Piperazinylalkyl)carbazoles as Bax-modulators

1978
- 1978-12-28 ZA ZA787352A patent/ZA787352B/xx unknown
1979
- 1979-10-29 PL PL1979219299A patent/PL128831B1/pl unknown
- 1979-10-29 PL PL1979241357A patent/PL138490B1/pl unknown
- 1979-10-31 JP JP14115479A patent/JPS5564585A/ja active Pending
- 1979-10-31 AT AT0704179A patent/AT377760B/de not_active IP Right Cessation
- 1979-10-31 CS CS7955482A patent/CS225849B2/cs unknown
- 1979-10-31 SU SU802836304K patent/SU1014469A3/ru active
- 1979-10-31 CS CS797407A patent/CS225817B2/cs unknown
- 1979-10-31 SU SU792836304A patent/SU1153826A3/ru active
- 1979-10-31 HU HU79WE607A patent/HU184705B/hu unknown
- 1979-11-01 KR KR1019790003818A patent/KR830001276A/ko not_active Ceased
1980
- 1980-12-08 SU SU803212057A patent/SU1060111A3/ru active

Also Published As

Publication number	Publication date
SU1060111A3 (ru)	1983-12-07
AT377760B (de)	1985-04-25
SU1153826A3 (ru)	1985-04-30
SU1014469A3 (ru)	1983-04-23
ATA704179A (de)	1984-09-15
HU184705B (en)	1984-10-29
KR830001276A (ko)	1983-04-30
PL128831B1 (en)	1984-03-31
ZA787352B (en)	1980-08-27
PL219299A1 (pl)	1980-12-01
JPS5564585A (en)	1980-05-15
CS225817B2 (en)	1984-02-13
PL138490B1 (en)	1986-09-30

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