DD292909A5 - Verfahren zur herstellung neuer 2-(1-piperazinyl)-4-phenylcycloalkanopyridinderivate - Google Patents

Verfahren zur herstellung neuer 2-(1-piperazinyl)-4-phenylcycloalkanopyridinderivate Download PDF

Info

Publication number: DD292909A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; formula; alkyl; piperazinyl; compounds
Prior art date: 1989-03-03

Application number

DD90338287A

Other languages

German (de)

English (en)

Inventor

Katsuhiko Hino

Naoki Kai

Masato Sakamoto

Tatsuya Kon

Makoto Oka

Kiyoshi Furukawa

Yoshiaki Ochi

Original Assignee

��@��@��Kk��Kk��

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.)

1989-03-03

Filing date

1990-03-01

Publication date

1991-08-14

1990-03-01 Application filed by ��@��@��Kk��Kk�� filed Critical ��@��@��Kk��Kk��

1991-08-14 Publication of DD292909A5 publication Critical patent/DD292909A5/de

Links

-1 1-PIPERAZINYL Chemical class 0.000 title claims description 76
238000004519 manufacturing process Methods 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 136
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 41
238000002360 preparation method Methods 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000005843 halogen group Chemical group 0.000 claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 5
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
229910014585 C2-Ce Inorganic materials 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 9
229940079593 drug Drugs 0.000 abstract description 8
125000002947 alkylene group Chemical group 0.000 abstract description 6
230000000561 anti-psychotic effect Effects 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
239000002249 anxiolytic agent Substances 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
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230000002490 cerebral effect Effects 0.000 abstract description 3
201000010099 disease Diseases 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 52
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CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 8
DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
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QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 8
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 8
ZTVXNUVIKIEUSZ-UHFFFAOYSA-N 2-(4-butylpiperazin-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine Chemical compound C1CN(CCCC)CCN1C1=CC(C=2C=CC(F)=CC=2)=C(CCCCCC2)C2=N1 ZTVXNUVIKIEUSZ-UHFFFAOYSA-N 0.000 description 7
206010047700 Vomiting Diseases 0.000 description 7
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011777 magnesium Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
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125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 6
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LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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150000003222 pyridines Chemical class 0.000 description 1
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230000002285 radioactive effect Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
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HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
229960004499 scopolamine hydrobromide Drugs 0.000 description 1
WTGQALLALWYDJH-MOUKNHLCSA-N scopolamine hydrobromide (anhydrous) Chemical compound Br.C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-MOUKNHLCSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035939 shock Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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238000003756 stirring Methods 0.000 description 1
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OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
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235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
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239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

DD90338287A 1989-03-03 1990-03-01 Verfahren zur herstellung neuer 2-(1-piperazinyl)-4-phenylcycloalkanopyridinderivate DD292909A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5254489		1989-03-03

Publications (1)

Publication Number	Publication Date
DD292909A5 true DD292909A5 (de)	1991-08-14

Family

ID=12917732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90338287A DD292909A5 (de)	1989-03-03	1990-03-01	Verfahren zur herstellung neuer 2-(1-piperazinyl)-4-phenylcycloalkanopyridinderivate

Country Status (14)

Country	Link
US (1)	US5021421A (fr)
EP (1)	EP0385237B1 (fr)
KR (1)	KR0149649B1 (fr)
AT (1)	ATE107922T1 (fr)
AU (1)	AU623981B2 (fr)
CA (1)	CA2011346C (fr)
DD (1)	DD292909A5 (fr)
DE (1)	DE69010232T2 (fr)
DK (1)	DK0385237T3 (fr)
ES (1)	ES2058630T3 (fr)
FI (1)	FI94413C (fr)
HU (1)	HU204810B (fr)
NO (1)	NO177095C (fr)
RU (1)	RU2075478C1 (fr)

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1990
- 1990-02-20 DK DK90103244.1T patent/DK0385237T3/da active
- 1990-02-20 DE DE69010232T patent/DE69010232T2/de not_active Expired - Lifetime
- 1990-02-20 ES ES90103244T patent/ES2058630T3/es not_active Expired - Lifetime
- 1990-02-20 AT AT90103244T patent/ATE107922T1/de not_active IP Right Cessation
- 1990-02-20 US US07/481,183 patent/US5021421A/en not_active Expired - Lifetime
- 1990-02-20 EP EP90103244A patent/EP0385237B1/fr not_active Expired - Lifetime
- 1990-03-01 DD DD90338287A patent/DD292909A5/de unknown
- 1990-03-01 FI FI901030A patent/FI94413C/fi active IP Right Grant
- 1990-03-01 NO NO900991A patent/NO177095C/no not_active IP Right Cessation
- 1990-03-01 AU AU50604/90A patent/AU623981B2/en not_active Expired
- 1990-03-02 CA CA002011346A patent/CA2011346C/fr not_active Expired - Lifetime
- 1990-03-02 HU HU901275A patent/HU204810B/hu unknown
- 1990-03-03 KR KR1019900002874A patent/KR0149649B1/ko not_active Expired - Lifetime
1992
- 1992-11-12 RU RU92004429/04A patent/RU2075478C1/ru active

Also Published As

Publication number	Publication date
HK1005872A1 (en)	1999-01-29
AU623981B2 (en)	1992-05-28
CA2011346A1 (fr)	1990-09-03
ATE107922T1 (de)	1994-07-15
EP0385237A2 (fr)	1990-09-05
HU204810B (en)	1992-02-28
DE69010232T2 (de)	1994-12-01
ES2058630T3 (es)	1994-11-01
EP0385237A3 (fr)	1991-03-20
HU901275D0 (en)	1990-05-28
DK0385237T3 (da)	1994-07-25
CA2011346C (fr)	1999-08-03
FI901030A0 (fi)	1990-03-01
FI94413C (fi)	1995-09-11
US5021421A (en)	1991-06-04
DE69010232D1 (de)	1994-08-04
RU2075478C1 (ru)	1997-03-20
NO900991L (no)	1990-09-04
HUT53361A (en)	1990-10-28
KR0149649B1 (ko)	1998-10-15
NO900991D0 (no)	1990-03-01
NO177095C (no)	1995-07-19
NO177095B (no)	1995-04-10
AU5060490A (en)	1990-09-06
FI94413B (fi)	1995-05-31
EP0385237B1 (fr)	1994-06-29
KR900014358A (ko)	1990-10-23

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