DE1695392A1 - Process for the preparation of piperazine derivatives - Google Patents

Process for the preparation of piperazine derivatives

Info

Publication number
DE1695392A1
DE1695392A1 DE19671695392 DE1695392A DE1695392A1 DE 1695392 A1 DE1695392 A1 DE 1695392A1 DE 19671695392 DE19671695392 DE 19671695392 DE 1695392 A DE1695392 A DE 1695392A DE 1695392 A1 DE1695392 A1 DE 1695392A1
Authority
DE
Germany
Prior art keywords
general formula
fluorophenyl
given above
meaning given
pyridyl
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
DE19671695392
Other languages
German (de)
Inventor
Norbert Busch
Roland-Yves Mauvernay
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of DE1695392A1 publication Critical patent/DE1695392A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

TitTit

«I«I.

d-d-

SlSl

1Ö953921Ö95392

M O) pHMO) pH

α> χα -ρ U Oα> χα -ρ U O

CLV/CLV /

COlCOl

Ja r 3 Yes r 3

CMCM

(Si(Si

CNiCNi

CMCM

CM.CM.

L/"L / "

if»if »

ϊ.ϊ.

Pharnakodyn. Wirkungen der Derivat« geaäß Tabelle XPharnakodyn. Effects of the derivative according to Table X

1B953921B95392

VerbinConnect akufe
Toxiziräfakufe
Toxiziräf Spnrwerz. \JirUuno Spnrwerz. \ JirUuno ohem. SHm.ohem. SHm. iruzund.iruzund. XX WiykuncWiykunc NAN / A WiVkg.WiVkg. dung
Wr- manure
Wr- 25002500 (al. Snm. (al. Snm. 150150 hemm. UvIq.inhibit UvIq. —- AA. INHIiLINHIiL α ZNSα CNS 11 75007500 770770 4040 inmiiii- "Jjinmiiii- "yy
328328 —- INHlB-INHlB- 8080 ■*- +■ * - + 22 20002000 5050 5050 485485 —- 8080 5050 + +++ ++ 33 >3000> 3000 8080 —- 262262 —- 6565 5050 44th >3000> 3000 ii 775775 772772 —- 6060 —- + •ί-+ • ί- 55 30003000 140140 ii 365365 —- —- 2020th 00 66th >3000> 3000 i . i . 200200 /3// 3 / 2626th 2020th —- 77th 500500 —- 2020th 286286 —- 1515th 3535 88th >300C> 300C 6060 ίί 245245 —- 4040 2222nd 00 99 15001500 ίί 62,562.5 703703 —- 4646 «— .«-. WW. >30Q0> 30Q0 730730 770770 250250 —- —- SOSO 1111 >3000> 3000 425425 5050 760760 INHiB. INHiB . 6060 1212th > 3000> 3000 7575 —- 359359 —- iiWEBS.iiWEBS. 5050 1313th >3000> 3000 Ki,Ki, ii 137137 —- 6060 5050 HH 20002000 —- 9090 —- —- 1616 7070 1515th >3000> 3000 WW. 474474 —- 8585 TOTO 1616 > 2500> 2500 3131 mm 353353 —- /Wv./ Wv. + + ++ + + 1717th 600600 WOWHERE ii —- 3434 —- 4040 1S1S > 3000> 3000 ii 8ZS8ZS 7171 —- «5«5 —- 1919th >3000> 3000 125125 —- 253253 —- —- 7777 ++++++ 2020th 16001600 210210 700700 7777 2525th 2323 3030th 2/2 / > 3000> 3000 250250 T75T75 753753 —- imin the 6262 2222nd > 2000> 2000 750750 3030th 240240 asas ++ 2323 20002000 — -- - 3030th 203203 —- 4242 -- 2424 >2O00> 2O00 120120 175175 367367 2828 7070 + + ++ + + 2525th 41S41S 700700 ii 774774 —- 3030th 8080 2626th 20002000 —- // 4040 8080 —- 4-4- 2727 >1000> 1000 200200 —- 4040 —- 2525th 25002500 425425 - — - - 3030th —- ++ 2929 13001300 ■ —■ - 8080 737737 —- — -- - soso + ++ + 3030th >W00> W00 —- —- 279279 8383 3)3) 15001500 —- 2525th 3232 10001000 —- 1515th + + ++ + + 3333 15001500 4040 —- 4343 4-+++4 - +++ 3434 400400 100100 3Z53Z5 392392 2828 7979 2727 3535 5050 —- SZSZ

TmhmlU t B«ispi«l« TmhmlU t B "ispi" l " Derivat·Derivative·

VerbinConnect
dungmanure ChCh OO ηη Β&*βΒ & * β Testp. , ,
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CC) Testp. ,,
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CC) 11 OO JJ -- 148148 22 OO 33 6767 160160 33 σ-σ- 33 7272 168168 44th ΟΟ «■ο«■ ο 22 112112 172172 SS. ο-ο- Q-CH-CHg-Q-CH-CHg- 33 8181 172172 66th ο-ο- Q-CiI-CH2-Q-CiI-CH 2 -
UC4H9(QUC 4 H 9 (Q 11 —- 158158 77th ο-ο- OCH2-OCH 2 - 33 —- 166166 SS. OO 33 -- 182182 99 Q-CH-CH2-Q-CH-CH 2 -
OCgH5 OCgH 5 22 101101 161161 1010 —- 153153

dungmanure
Nr.No. CH3O^CH 3 O ^ R2 R 2 ηη «sip.«Sip.
Basebase
fT.)fT.) fest/*
Dichiorhvm
(0C) fixed/*
Dichiorhvm
( 0 C) 1111 CH3O,CH 3 O,
CH3(TCH 3 (T. OO 22 103103 162162 1212th CH3OkCH 3 OK
CH3O^CH 3 O ^ OO 33 __ 165165 7575 CH3(T^CH 3 (T ^ 22 116116 170170 7474 CH3O s^CH 3 O s ^ <£-<£ - 22 112112 161161 1515th CH9O,CH 9 O,
CH5O-TyCH 5 O-Ty
CH3O^CH 3 O ^ F<y F <y 33 —- 169169 1616 CH3OCH 3 O
CH3O-CyCH 3 O-Cy
CH3O^CH 3 O ^ (S(P 33 8787 167167 1717th Q-CH-CH2-Q-CH-CH 2 -
OCHiOCHi '' -- mm 1818th CH3OCH 3 O Q-CH-CH2-Q-CH-CH 2 -
QCH3 QCH 3 22 -- 172172 1919th CH3O,CH 3 O,
CH3<yCH 3 <y Q-CH-CH2-Q-CH-CH 2 -
OC2H5 OC 2 H 5 -- 176176 2020th Q-CH-CH2-Q-CH-CH 2 -
OC4H9C1)OC 4 H 9 C 1 ) —- 161161

VDVD

cn co cn co cn co cn co

Claims (2)

- 13 Patentansprüche- 13 claims 1. Verfahren zur Herstellung neuer cheraiseher> Verbindungen, insbesondere zur Verwendung als entzündungshemmende und schmerzstillende Arzneimittel der allgemeinen Formel1. Method of making new cheraiseher> Compounds, in particular for use as anti-inflammatory and analgesic medicaments of the general formula - (GVn- (G Vn in derin the H1 \ Phenyl-, 4-Fluorphenyl-, Trimethoxyphenyl-, Furanyl-,H 1 \ phenyl, 4-fluorophenyl, trimethoxyphenyl, furanyl, Thiophenyl-, 3-Pyridyl- und 4-Pyridyl- bedeutet und fip : Phenyl-, 4-Chlorphenyl-, 2-Fluorphenyl-, 4-Fluorphenyl-, üenzyl- sowie eine Gruppe der allgemeinen FormelThiophenyl-, 3-pyridyl- and 4-pyridyl- means and fip: phenyl, 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, üenzyl- and a group of the general formula G6H5 - CH - GH2 OR G 6 H 5 - CH - GH 2 OR (worin H eine niedere Alkylgruppe, insbesondere Methyl-, Äthyl-r und Xsobutyl- ist) bedeutet,(where H is a lower alkyl group, especially methyl-, ethyl- r and xsobutyl-), wobei η eine ganze Zahl von 1 bis 3 ist, dadurch g e k β η η ■ zeichnet, daß man ein substituiertes Piperazin der allgemeinen B'ormelwhere η is an integer from 1 to 3, thereby g e k β η η ■ draws that a substituted piperazine of the general B'ormel : H ■"■."■ ■-■.--..- ι : H ■ "■." ■ ■ - ■. - ..- ι -■*4 109815/2189 - ■ * 4 109815/2189 Ί695392Ί695392 in der R„ die oben angegebene Bedeutung hat, mit einem 1,2,^- Oxadiazolderivat der allgemeinen Formelin which R "has the meaning given above, with a 1,2, ^ - Oxadiazole derivative of the general formula R1 R 1 ' in der R. die oben angegebene Bedeutung hat und η eine ganze
Zahl-von 1 bis 3 ist, umsetzt.'in the R. has the meaning given above and η a whole
Number-from 1 to 3 is implemented. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dai3 man bei η = 2 das Piperazinderivat anstelle mit dem 1,2,^-Oxadiazol mit einem entsprechenden Acryloylamidoxim der allgemeinen Formel2. The method according to claim 1, characterized in that one dai3 at η = 2 the piperazine derivative instead of the 1,2, ^ - oxadiazole with a corresponding acryloylamidoxime of the general formula GH2 = CH - G - 0GH 2 = CH - G - 0 G ιG ι in der R^ die oben angegebene Bedeutung hat, in siedendem
Toluol umsetzt. in which R ^ has the meaning given above, in boiling
Toluene converts. 109815/2189109815/2189
DE19671695392 1966-02-16 1967-02-10 Process for the preparation of piperazine derivatives Pending DE1695392A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MC608A MC598A1 (en) 1966-02-16 1966-02-16 New chemical compounds and process for their preparation

Publications (1)

Publication Number Publication Date
DE1695392A1 true DE1695392A1 (en) 1971-04-08

Family

ID=19737671

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19671695392 Pending DE1695392A1 (en) 1966-02-16 1967-02-10 Process for the preparation of piperazine derivatives

Country Status (7)

Country Link
CH (1) CH478141A (en)
DE (1) DE1695392A1 (en)
ES (1) ES336777A1 (en)
FR (1) FR6671M (en)
GB (1) GB1110360A (en)
MC (1) MC598A1 (en)
NL (1) NL6702283A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005061427A1 (en) * 2005-12-22 2007-06-28 Grünenthal GmbH New 1-aminomethyl-4-oxadiazolylalkyl-cyclohexane derivatives, useful for treating e.g. pain, depression and urinary incontinence, bind to mu-opioid receptors and inhibit reuptake of serotonin and noradrenaline

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3005287A1 (en) * 1980-02-13 1981-08-20 Basf Ag, 6700 Ludwigshafen PHENYLPIPERAZINE DERIVATIVES OF 1,3,4-OXADIAZOLYLPHENOLS, THEIR PRODUCTION AND THERAPEUTIC AGENTS CONTAINING THEM
JP4881725B2 (en) * 2003-04-09 2012-02-22 エクセリクシス， インク． TIE-2 modulator and usage
GB0510139D0 (en) 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds B1

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005061427A1 (en) * 2005-12-22 2007-06-28 Grünenthal GmbH New 1-aminomethyl-4-oxadiazolylalkyl-cyclohexane derivatives, useful for treating e.g. pain, depression and urinary incontinence, bind to mu-opioid receptors and inhibit reuptake of serotonin and noradrenaline

Also Published As

Publication number Publication date
NL6702283A (en) 1967-08-17
ES336777A1 (en) 1968-06-01
GB1110360A (en) 1968-04-18
CH478141A (en) 1969-09-15
MC598A1 (en) 1967-03-21
FR6671M (en) 1969-02-03

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