NO123245B - - Google Patents

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Info

Publication number: NO123245B
Authority: NO; Norway
Prior art keywords: piperazine; benzhydryl; ethyl; hydroxyethoxy; boiling point
Prior art date: 1966-06-02

Application number

NO16839667A

Other languages

English (en)

Norwegian (no)

Inventor

J Crawford

J Getson

R Chadha

R Lewis

Original Assignee

Stauffer Wacke Silicone Corp

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.)

1966-06-02

Filing date

1967-05-31

Publication date

1971-10-18

1967-05-31 Application filed by Stauffer Wacke Silicone Corp filed Critical Stauffer Wacke Silicone Corp

1971-10-18 Publication of NO123245B publication Critical patent/NO123245B/no

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000004885 piperazines Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical class C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002366 halogen compounds Chemical class 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
230000004048 modification Effects 0.000 claims 6
238000012986 modification Methods 0.000 claims 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 127
238000009835 boiling Methods 0.000 description 49
-1 1-p-bromobenzhydryl-4-[2-(2-hydroxyethoxy)-ethyl]-piperazine Chemical compound 0.000 description 41
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
239000002585 base Substances 0.000 description 24
239000000243 solution Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229960005141 piperazine Drugs 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
239000000203 mixture Substances 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
238000004821 distillation Methods 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000008096 xylene Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007859 condensation product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
RMXZOOYQUFHRPE-UHFFFAOYSA-N 1-[(4-bromophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 RMXZOOYQUFHRPE-UHFFFAOYSA-N 0.000 description 3
LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 3
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
KECMLGZOQMJIBM-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCCl KECMLGZOQMJIBM-UHFFFAOYSA-N 0.000 description 2
GYCLKODXTAIUAY-UHFFFAOYSA-N 2-[2-(2-piperazin-1-ylethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCN1CCNCC1 GYCLKODXTAIUAY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical class OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
229960002327 chloral hydrate Drugs 0.000 description 2
239000000155 melt Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
FLNQAPQQAZVRDA-UHFFFAOYSA-N 1-(2-(2-Hydroxyethoxy)ethyl)piperazine Chemical compound OCCOCCN1CCNCC1 FLNQAPQQAZVRDA-UHFFFAOYSA-N 0.000 description 1
YMXAYMSJCVGYEM-UHFFFAOYSA-N 1-Chloro-2-(chlorophenylmethyl)benzene Chemical compound C=1C=CC=C(Cl)C=1C(Cl)C1=CC=CC=C1 YMXAYMSJCVGYEM-UHFFFAOYSA-N 0.000 description 1
JHKFGCFYIKPSJX-UHFFFAOYSA-N 1-[(2-bromophenyl)-phenylmethyl]piperazine Chemical compound BrC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 JHKFGCFYIKPSJX-UHFFFAOYSA-N 0.000 description 1
RLZPNIGECDMAJH-UHFFFAOYSA-N 1-[(2-chlorophenyl)-phenylmethyl]piperazine Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 RLZPNIGECDMAJH-UHFFFAOYSA-N 0.000 description 1
IZNRYBFUKJNNLH-UHFFFAOYSA-N 1-[(2-methylphenyl)-phenylmethyl]piperazine Chemical compound CC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 IZNRYBFUKJNNLH-UHFFFAOYSA-N 0.000 description 1
YNZQUVOSFLCDGV-UHFFFAOYSA-N 1-[(3-bromophenyl)-phenylmethyl]piperazine Chemical compound BrC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 YNZQUVOSFLCDGV-UHFFFAOYSA-N 0.000 description 1
UGTBQURRNOQZSV-UHFFFAOYSA-N 1-[(3-chlorophenyl)-phenylmethyl]piperazine Chemical compound ClC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 UGTBQURRNOQZSV-UHFFFAOYSA-N 0.000 description 1
KMXMAWICRXKQFE-UHFFFAOYSA-N 1-[(3-methoxyphenyl)-phenylmethyl]piperazine Chemical compound COC1=CC=CC(C(N2CCNCC2)C=2C=CC=CC=2)=C1 KMXMAWICRXKQFE-UHFFFAOYSA-N 0.000 description 1
JYNPNQFAXHCTBV-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-3-methoxybenzene Chemical compound COC1=CC=CC(C(Cl)C=2C=CC=CC=2)=C1 JYNPNQFAXHCTBV-UHFFFAOYSA-N 0.000 description 1
CFPYBVHEZBNWTR-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-3-methylbenzene Chemical compound CC1=CC=CC(C(Cl)C=2C=CC=CC=2)=C1 CFPYBVHEZBNWTR-UHFFFAOYSA-N 0.000 description 1
GHBNCXLSRVICCO-UHFFFAOYSA-N 1-bromo-2-[chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=C(Br)C=1C(Cl)C1=CC=CC=C1 GHBNCXLSRVICCO-UHFFFAOYSA-N 0.000 description 1
DNRHPNFMEIEGMA-UHFFFAOYSA-N 1-bromo-3-[chloro(phenyl)methyl]benzene Chemical compound C=1C=CC(Br)=CC=1C(Cl)C1=CC=CC=C1 DNRHPNFMEIEGMA-UHFFFAOYSA-N 0.000 description 1
NOMHRYCAVGPGEC-UHFFFAOYSA-N 1-bromo-4-[chloro(phenyl)methyl]benzene Chemical compound C=1C=C(Br)C=CC=1C(Cl)C1=CC=CC=C1 NOMHRYCAVGPGEC-UHFFFAOYSA-N 0.000 description 1
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229920005557 bromobutyl Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VUFOCTSXHUWGPW-UHFFFAOYSA-N etodroxizine Chemical compound C1CN(CCOCCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 VUFOCTSXHUWGPW-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
150000002680 magnesium Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960003506 piperazine hexahydrate Drugs 0.000 description 1
AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Silicon Polymers (AREA)
Compositions Of Macromolecular Compounds (AREA)
Graft Or Block Polymers (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO16839667A 1966-06-02 1967-05-31 NO123245B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US55468366A	1966-06-02	1966-06-02

Publications (1)

Publication Number	Publication Date
NO123245B true NO123245B (de)	1971-10-18

Family

ID=24214293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO16839667A NO123245B (de)	1966-06-02	1967-05-31

Country Status (7)

Country	Link
BR (1)	BR6790060D0 (de)
CH (1)	CH553836A (de)
DE (1)	DE1694973C3 (de)
GB (1)	GB1169605A (de)
IL (1)	IL27997A (de)
NO (1)	NO123245B (de)
SE (1)	SE354475B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3030195A1 (de) *	1980-08-09	1982-04-08	Bayer Ag, 5090 Leverkusen	Bei raumtemperatur vernetzbare pfropfpolymerisat-dispersionen
DE3105499A1 (de) *	1981-02-14	1982-09-02	Bayer Ag, 5090 Leverkusen	Stabile, organische mehrkomponentendispersionen
US4797501A (en) *	1986-12-31	1989-01-10	Union Carbide Corporation	Silicone-based stabilizers useful in the preparation of improved polyurethane foams
DE102006059295B4 (de) *	2006-12-11	2009-12-17	Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh	Hydrolysierte silangepfropfte Olefinhomo- und(block)copolymere sowie Verfahren zu ihrer Herstellung
CN102964983B (zh) *	2012-12-12	2015-01-07	广州市高士实业有限公司	一种硅杂化复合涂覆电子胶及其制备方法

1967
- 1967-05-17 IL IL2799767A patent/IL27997A/en unknown
- 1967-05-24 GB GB2408167A patent/GB1169605A/en not_active Expired
- 1967-05-31 NO NO16839667A patent/NO123245B/no unknown
- 1967-06-01 BR BR19006067A patent/BR6790060D0/pt unknown
- 1967-06-01 DE DE19671694973 patent/DE1694973C3/de not_active Expired
- 1967-06-02 CH CH782667A patent/CH553836A/de not_active IP Right Cessation
- 1967-06-02 SE SE775067A patent/SE354475B/xx unknown

Also Published As

Publication number	Publication date
SE354475B (de)	1973-03-12
IL27997A (en)	1971-07-28
BR6790060D0 (pt)	1973-01-16
DE1694973A1 (de)	1971-12-30
CH553836A (de)	1974-09-13
GB1169605A (en)	1969-11-05
DE1694973C3 (de)	1975-05-07
DE1694973B2 (de)	1974-09-05

Publication	Publication Date	Title
NO162965B (no)	1989-12-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater.
NO144514B (no)	1981-06-09	Skaftbefestigelse for husholdnings- og haveredskaper
DK174289B1 (da)	2002-11-18	Fremgangsmåde til fremstilling af 2-[2-[4-[(4-chlorphenyl)phenylmethyl]-1-piperazinyl]ethoxy]eddikesyre og dens dihydrochlorid
US2899436A (en)	1959-08-11	chjch
SE447257B (sv)	1986-11-03	Forfarande for framstellning av n-(2-pyrimidinyl)-piperazinylalkyl-azaspiroalkandioner
NO153530B (no)	1985-12-30	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte heterocykliske benzamider.
NO123245B (de)	1971-10-18
EP1971585B1 (de)	2011-03-09	Verfahren zur herstellung eines pharmazeutischen zwischenprodukts
NO151348B (no)	1984-12-17	Trikot stroempebukse og fremgangsmaate for fremstilling av samme
NO137965B (no)	1978-02-20	Analogifremgangsm}te for fremstilling av nye cykliske terapeutisk aktive urinstoffderivater og salter av disse med farmas¦ytisk akseptable syrer
NO118495B (de)	1970-01-05
NO138338B (no)	1978-05-08	Fremgangsmaate til fremstilling av tresponplater med kondensasjonsharpikser som bindemiddel
NO115944B (de)	1968-12-30
SU530644A3 (ru)	1976-09-30	Способ получени производных бензгидрил- -п-оксибензилпиперазина или их солей
NO143902B (no)	1981-01-26	Fenyl-lavere alkanoylaminer for bruk til fremstilling av terapeutisk virksomme fenyl-lavere-alkylaminer
US3002976A (en)	1961-10-03	1-(2-thienyl)-omega-(4-arylpiperazine)alkanols
NO147838B (no)	1983-03-14	Mellomprodukt til bruk ved fremstilling av det hypotensive middel 2-(4-(2-furoyl)piperazin-1-yl)-4-amino-6,7-dimetoksykinazolin
US2442865A (en)	1948-06-08	Heteboctcuc substituted fhenacxl
US3280196A (en)	1966-10-18	Benzhydryl-dihaloalkane ethers
JP4234206B2 (ja)	2009-03-04	テトラヒドロピリジン誘導体を調製する方法
NO116853B (de)	1969-06-02
NO150553B (no)	1984-07-30	Oppblaasbar baat
SK10182002A3 (sk)	2003-03-04	Spôsob výroby heterocyklických zlúčenín
GB808636A (en)	1959-02-11	Basically substituted heterocyclic compounds
US2870148A (en)	1959-01-20	Heterocyclic amides of n aralkyl piperidine carboxylic acids