CH513892A - Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetrahydroisochinolinen - Google Patents

Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetrahydroisochinolinen

Info

Publication number: CH513892A
Authority: CH; Switzerland
Prior art keywords: hydroxy; pyridyl; formula; tetrahydroisoquinolines; different
Prior art date: 1967-03-10

Application number

CH336568A

Other languages

German (de)

English (en)

Inventor

Wolfhard Dr Engel

Ernst Dr Seeger

Helmut Dr Teufel

Hans Dr Machleidt

Original Assignee

Thomae Gmbh Dr K

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.)

1967-03-10

Filing date

1968-03-07

Publication date

1971-10-15

1968-03-07 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1968-03-07 Priority to CH352671A priority Critical patent/CH514613A/de

1971-10-15 Publication of CH513892A publication Critical patent/CH513892A/de

Links

JKXJKPLJDNPYGT-UHFFFAOYSA-N 2-hydroxy-1-pyridin-2-yl-3,4,4a,5-tetrahydro-1H-isoquinoline Chemical class ON1C(C2=CC=CCC2CC1)C1=NC=CC=C1 JKXJKPLJDNPYGT-UHFFFAOYSA-N 0.000 title abstract description 3
239000002253 acid Substances 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 4
230000001754 anti-pyretic effect Effects 0.000 abstract description 2
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
150000003440 styrenes Chemical class 0.000 abstract description 2
240000004808 Saccharomyces cerevisiae Species 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
239000002260 anti-inflammatory agent Substances 0.000 abstract 1
230000001741 anti-phlogistic effect Effects 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
125000003039 tetrahydroisoquinolinyl group Chemical class C1(NCCC2=CC=CC=C12)* 0.000 abstract 1
239000000203 mixture Substances 0.000 description 11
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
OFYLBLSSPQTTHT-YVMONPNESA-N (NZ)-N-(pyridin-4-ylmethylidene)hydroxylamine Chemical compound O\N=C/C1=CC=NC=C1 OFYLBLSSPQTTHT-YVMONPNESA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 4
SYSWUIYSHHTQQA-UHFFFAOYSA-N CC1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)C Chemical compound CC1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)C SYSWUIYSHHTQQA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
-1 alkyl radicals Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
YMKBSXVBAHEQHF-UHFFFAOYSA-N (2-chloro-2-methylpropyl)benzene Chemical compound CC(C)(Cl)CC1=CC=CC=C1 YMKBSXVBAHEQHF-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-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
239000002841 Lewis acid Substances 0.000 description 2
MTFJSAGADRTKCI-UHFFFAOYSA-N N-(pyridin-2-ylmethylidene)hydroxylamine Chemical class ON=CC1=CC=CC=N1 MTFJSAGADRTKCI-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
YBKOPFQCLSPTPV-YVMONPNESA-N (nz)-n-(pyridin-3-ylmethylidene)hydroxylamine Chemical compound O\N=C/C1=CC=CN=C1 YBKOPFQCLSPTPV-YVMONPNESA-N 0.000 description 1
FSXAUFIRAAFYLY-UHFFFAOYSA-N 2-hydroxy-3,3,4-trimethyl-1-pyridin-4-yl-1,4-dihydroisoquinoline 2-methyl-1-(4-methylphenyl)propan-2-ol Chemical compound ON1C(C2=CC=CC=C2C(C1(C)C)C)C1=CC=NC=C1.CC1=CC=C(CC(C)(C)O)C=C1 FSXAUFIRAAFYLY-UHFFFAOYSA-N 0.000 description 1
GYKAIFVYOWINSJ-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-1-pyridin-3-yl-1,4-dihydroisoquinoline 2-methyl-1-phenylpropan-2-ol Chemical compound CC1(N(C(C2=CC=CC=C2C1)C=1C=NC=CC1)O)C.C(C1=CC=CC=C1)C(C)(C)O GYKAIFVYOWINSJ-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
FTZBYXCNXOPJEL-UHFFFAOYSA-N 2-methyl-1-phenylbutan-2-ol Chemical compound CCC(C)(O)CC1=CC=CC=C1 FTZBYXCNXOPJEL-UHFFFAOYSA-N 0.000 description 1
BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
MXTNFIYGTWARIN-UHFFFAOYSA-N 2-methylprop-2-enylbenzene Chemical compound CC(=C)CC1=CC=CC=C1 MXTNFIYGTWARIN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VXSLZYONEMVQRB-UHFFFAOYSA-N 3-benzylpentan-3-ol Chemical compound CCC(O)(CC)CC1=CC=CC=C1 VXSLZYONEMVQRB-UHFFFAOYSA-N 0.000 description 1
RKOLMNVODUFJFL-UHFFFAOYSA-N C(C)C1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)C Chemical compound C(C)C1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)C RKOLMNVODUFJFL-UHFFFAOYSA-N 0.000 description 1
HXEDTLAHHGHXGP-UHFFFAOYSA-N C(C)C1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)CC Chemical compound C(C)C1(N(C(C2=CC=CC=C2C1)C1=CC=NC=C1)O)CC HXEDTLAHHGHXGP-UHFFFAOYSA-N 0.000 description 1
BDUOKWFPSVIXQO-UHFFFAOYSA-N CC1(N(C(C2=CC=CC=C2C1)C1=NC=CC=C1)O)C Chemical compound CC1(N(C(C2=CC=CC=C2C1)C1=NC=CC=C1)O)C BDUOKWFPSVIXQO-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000002265 Human Growth Hormone Human genes 0.000 description 1
108010000521 Human Growth Hormone Proteins 0.000 description 1
239000000854 Human Growth Hormone Substances 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
OIKGFMHISSQNRL-UHFFFAOYSA-N N-[(6-methylpyridin-2-yl)methylidene]hydroxylamine Chemical compound CC1=CC=CC(C=NO)=N1 OIKGFMHISSQNRL-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 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
230000004913 activation Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229940063153 saizen Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material 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)

CH336568A 1967-03-10 1968-03-07 Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetrahydroisochinolinen CH513892A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH352671A CH514613A (de)	1967-03-10	1968-03-07	Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetra-hydroisochinolinen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DET0033403		1967-03-10

Publications (1)

Publication Number	Publication Date
CH513892A true CH513892A (de)	1971-10-15

Family

ID=7557741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH336568A CH513892A (de)	1967-03-10	1968-03-07	Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetrahydroisochinolinen

Country Status (8)

Country	Link
AT (1)	AT278798B (fr)
CH (1)	CH513892A (fr)
DE (1)	DE1695887A1 (fr)
DK (1)	DK120081B (fr)
ES (1)	ES351411A1 (fr)
FR (2)	FR1555417A (fr)
NL (2)	NL6803136A (fr)
SE (1)	SE328573B (fr)

0
- NL NL130539D patent/NL130539C/xx active
1967
- 1967-03-10 DE DE19671695887 patent/DE1695887A1/de active Pending
1968
- 1968-02-23 AT AT175368A patent/AT278798B/de not_active IP Right Cessation
- 1968-03-06 NL NL6803136A patent/NL6803136A/xx unknown
- 1968-03-07 CH CH336568A patent/CH513892A/de not_active IP Right Cessation
- 1968-03-08 FR FR1555417D patent/FR1555417A/fr not_active Expired
- 1968-03-08 DK DK98468A patent/DK120081B/da unknown
- 1968-03-08 SE SE314568A patent/SE328573B/xx unknown
- 1968-03-09 ES ES351411A patent/ES351411A1/es not_active Expired
- 1968-06-07 FR FR154235A patent/FR8072M/fr not_active Expired

Also Published As

Publication number	Publication date
NL130539C (fr)
NL6803136A (fr)	1968-09-11
SE328573B (fr)	1970-09-21
DK120081B (da)	1971-04-05
FR1555417A (fr)	1969-01-24
FR8072M (fr)	1970-07-15
ES351411A1 (es)	1969-06-01
DE1695887A1 (de)	1971-05-06
AT278798B (de)	1970-02-10

Legal Events

Date	Code	Title	Description
1974-10-15	PL	Patent ceased

Publication	Publication Date	Title
DE2115718A1 (de)	1971-10-14	Verfahren zur Herstellung von penta cyclischen Alkaloiden
AT391866B (de)	1990-12-10	Verfahren zur herstellung neuer s-triazolo (1,5-a) pyrimidine
DE1232138B (de)	1967-01-12	Verfahren zur Herstellung von delta 5-6-Methylsteroiden
CH513892A (de)	1971-10-15	Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetrahydroisochinolinen
DE889446C (de)	1953-09-10	Verfahren zur Herstellung von Phenanthrolin-5, 6-chinonen
CH514613A (de)	1971-10-31	Verfahren zur Herstellung von 2-Hydroxy-1-(pyridyl)-tetra-hydroisochinolinen
AT215422B (de)	1961-06-12	Verfahren zur Herstellung von neuen Pyridazin-Derivaten
DE1137025B (de)	1962-09-27	Verfahren zur Herstellung von Phenthiazinderivaten
AT282629B (de)	1970-07-10	Verfahren zur herstellung neuer zimtsaeureamide
DE2004743A1 (de)	1970-09-03	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE1924451C3 (de)	1976-05-06	Verfahren zur Herstellung von 2-Methylamino-5-phenyl-3H-1,4benzodiazepin-4-oxydderivaten
AT275525B (de)	1969-10-27	Verfahren zur Herstellung von neuen Pyridyl-dihydroisochinolinen und von deren Salzen
DE1695080A1 (de)	1970-12-10	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen
AT203491B (de)	1959-05-25	Verfahren zur Herstellung von neuen 3,5-Diketo-pyrazolidin-Derivaten
AT273970B (de)	1969-09-10	Verfahren zur Herstellung von neuen, in 1-Stellung mit einem 3- oder 4-Pyridylrest substituierten, 3,3-disubstituierten 3,4-Dihydroisochinolinen
AT206899B (de)	1959-12-28	Verfahren zur Herstellung von neuen, substituierten 3,5-Dioxo-tetrahydro-1,2,6-thiadiazin-1,1-dioxyden
DE1445184C (de)	1972-05-18	Verfahren zur Herstellung von alpha-Pyrrolidino-n-valerophenonen und ihren Salzen
AT218519B (de)	1961-12-11	Verfahren zur Herstellung von neuen Pyrazol-Derivaten
DE1088059B (de)	1960-09-01	Verfahren zur Herstellung von in 1- und 9-Stellung substituierten, quaternaeren ª†-Carboliniumsalzen
DE1190464B (de)	1965-04-08	Verfahren zur Herstellung von Pyridinderivaten
DE1126883B (de)	1962-04-05	Verfahren zur Herstellung von 1-Aminoalkyl-7-aza-benzimidazolen
DE1287581B (de)	1969-01-23	Verfahren zur Herstellung von 2-(Pyridyl)-2, 3-dihydro-1, 3-benzoxazin-4-on-derivaten
CH517747A (de)	1972-01-15	Verfahren zur Herstellung neuer Indenopyridinderivate
CH517745A (de)	1972-01-15	Verfahren zur Herstellung neuer Indenopyridinderivate
CH517746A (de)	1972-01-15	Verfahren zur Herstellung neuer Indenopyridinderivate