DD146951A5 - Verfahren zur herstellung von neuen derivaten von dimeren des isoeugenols - Google Patents

Verfahren zur herstellung von neuen derivaten von dimeren des isoeugenols Download PDF

Info

Publication number: DD146951A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroxy; methyl; methoxy; hydroxyethyl; group
Prior art date: 1978-11-15

Application number

DD79216856A

Other languages

German (de)

English (en)

Inventor

Herfried Griengl

Gabriele Foidl

Original Assignee

Plc Pharma Licences

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.)

1978-11-15

Filing date

1979-11-13

Publication date

1981-03-11

1979-11-13 Application filed by Plc Pharma Licences filed Critical Plc Pharma Licences

1981-03-11 Publication of DD146951A5 publication Critical patent/DD146951A5/de

Links

239000000539 dimer Substances 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 9
ITDOFWOJEDZPCF-UHFFFAOYSA-N dl-Dehydrodiisoeugenol Natural products O1C=2C(OC)=CC(C=CC)=CC=2C(C)C1C1=CC=C(O)C(OC)=C1 ITDOFWOJEDZPCF-UHFFFAOYSA-N 0.000 claims abstract description 17
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 16
BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims abstract description 11
BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 claims abstract description 11
BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
QSYFPBASFNGQSF-UHFFFAOYSA-N 1-ethyl-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methyl-2,3-dihydro-1h-inden-5-ol Chemical compound C12=CC(O)=C(OC)C=C2C(CC)C(C)C1C1=CC=C(O)C(OC)=C1 QSYFPBASFNGQSF-UHFFFAOYSA-N 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 7
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims abstract description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
-1 2,3-dihydro-7-methoxy-3-methyl-5- (E) -propenylbenzofuran-2-yl Chemical group 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 17
ITDOFWOJEDZPCF-AATRIKPKSA-N 2-methoxy-4-[7-methoxy-3-methyl-5-[(e)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol Chemical compound O1C=2C(OC)=CC(\C=C\C)=CC=2C(C)C1C1=CC=C(O)C(OC)=C1 ITDOFWOJEDZPCF-AATRIKPKSA-N 0.000 claims description 13
ITDOFWOJEDZPCF-CWTRNNRKSA-N Dehydro-diisoeugenol Natural products COC1=CC(=CC=2[C@H]([C@@H](OC=21)C1=CC(=C(C=C1)O)OC)C)C=CC ITDOFWOJEDZPCF-CWTRNNRKSA-N 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
FNKSTXGVEUSZJJ-UHFFFAOYSA-N 3-methyl-1,3-oxazolidine Chemical compound CN1CCOC1 FNKSTXGVEUSZJJ-UHFFFAOYSA-N 0.000 claims description 3
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229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
LJMBYOFLHIOEGO-UHFFFAOYSA-N 3-butyl-1,3-oxazolidine Chemical compound CCCCN1CCOC1 LJMBYOFLHIOEGO-UHFFFAOYSA-N 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
UBWJATJZTCPLPK-UHFFFAOYSA-N 3-ethyl-2-propan-2-yl-1,3-oxazolidine Chemical compound CCN1CCOC1C(C)C UBWJATJZTCPLPK-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 claims description 2
229960000649 oxyphenbutazone Drugs 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims 2
AJMLLZSBIZWNEJ-SNAWJCMRSA-N 2-methoxy-3-methyl-5-[(E)-prop-1-enyl]-1-benzofuran Chemical compound COC=1OC2=C(C=1C)C=C(C=C2)\C=C\C AJMLLZSBIZWNEJ-SNAWJCMRSA-N 0.000 claims 1
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims 1
239000005770 Eugenol Substances 0.000 claims 1
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238000004519 manufacturing process Methods 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
101150109310 msrAB1 gene Proteins 0.000 abstract 1
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NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000004617 sleep duration Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007655 standard test method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical class OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD79216856A 1978-11-15 1979-11-13 Verfahren zur herstellung von neuen derivaten von dimeren des isoeugenols DD146951A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT0815178A AT371453B (de)	1978-11-15	1978-11-15	Verfahren zur herstellung von neuen derivaten des trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl) -7-methoxy-3-methyl-5-(e)-propenylbenzofurans

Publications (1)

Publication Number	Publication Date
DD146951A5 true DD146951A5 (de)	1981-03-11

Family

ID=3603009

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79216856A DD146951A5 (de)	1978-11-15	1979-11-13	Verfahren zur herstellung von neuen derivaten von dimeren des isoeugenols

Country Status (23)

Country	Link
US (1)	US4256764A (cs)
EP (1)	EP0011598B1 (cs)
JP (1)	JPS5572183A (cs)
AT (1)	AT371453B (cs)
AU (1)	AU525210B2 (cs)
CA (1)	CA1141392A (cs)
CS (1)	CS209828B2 (cs)
DD (1)	DD146951A5 (cs)
DE (1)	DE2964628D1 (cs)
DK (1)	DK478979A (cs)
ES (1)	ES485595A0 (cs)
FI (1)	FI793273A7 (cs)
GR (1)	GR72529B (cs)
HU (1)	HU180037B (cs)
IE (1)	IE48698B1 (cs)
IL (1)	IL58375A (cs)
NO (1)	NO152784C (cs)
NZ (1)	NZ191718A (cs)
PL (1)	PL219615A1 (cs)
PT (1)	PT70455A (cs)
SU (1)	SU963466A3 (cs)
YU (1)	YU271679A (cs)
ZA (1)	ZA795022B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR112012025740B1 (pt) *	2010-04-08	2017-12-26	Symrise Ag	Cosmetic preparation, and use of dihydrodesidrodi-isoeugenol
FR3073223B1 (fr) *	2017-11-07	2019-11-15	Arianegroup Sas	Composes biphenyles pluriepoxydes, preparation et utilisations

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1138042B (de) *	1959-11-25	1962-10-18	Ciba Geigy	Verfahren zur Herstellung von 1, 3, 3-Trimethyl-1-(p-hydroxyphenyl)-indanol-(6)
LU71012A1 (cs) *	1974-09-26	1976-08-19
DE2812664A1 (de) *	1978-03-22	1979-09-27	Plc Pharma Licences	Verwendung von dilignolen und dilignolaehnlichen verbindungen als wirkstoffe von lebertherapeutica

1978
- 1978-11-15 AT AT0815178A patent/AT371453B/de not_active IP Right Cessation
1979
- 1979-09-21 ZA ZA00795022A patent/ZA795022B/xx unknown
- 1979-09-21 AU AU51097/79A patent/AU525210B2/en not_active Ceased
- 1979-10-01 IE IE1863/79A patent/IE48698B1/en unknown
- 1979-10-01 NZ NZ191718A patent/NZ191718A/xx unknown
- 1979-10-01 US US06/080,552 patent/US4256764A/en not_active Expired - Lifetime
- 1979-10-03 IL IL58375A patent/IL58375A/xx unknown
- 1979-10-08 EP EP79810118A patent/EP0011598B1/de not_active Expired
- 1979-10-08 DE DE7979810118T patent/DE2964628D1/de not_active Expired
- 1979-10-17 GR GR60291A patent/GR72529B/el unknown
- 1979-10-22 FI FI793273A patent/FI793273A7/fi not_active Application Discontinuation
- 1979-10-30 HU HU79PA1366A patent/HU180037B/hu unknown
- 1979-10-31 ES ES485595A patent/ES485595A0/es active Granted
- 1979-11-01 NO NO793518A patent/NO152784C/no unknown
- 1979-11-06 YU YU02716/79A patent/YU271679A/xx unknown
- 1979-11-07 CS CS797598A patent/CS209828B2/cs unknown
- 1979-11-09 CA CA000339604A patent/CA1141392A/en not_active Expired
- 1979-11-13 DD DD79216856A patent/DD146951A5/de unknown
- 1979-11-13 JP JP14698979A patent/JPS5572183A/ja active Pending
- 1979-11-13 DK DK478979A patent/DK478979A/da not_active Application Discontinuation
- 1979-11-14 SU SU792839008A patent/SU963466A3/ru active
- 1979-11-14 PL PL21961579A patent/PL219615A1/xx unknown
- 1979-11-14 PT PT70455A patent/PT70455A/pt unknown

Also Published As

Publication number	Publication date
JPS5572183A (en)	1980-05-30
PL219615A1 (cs)	1980-08-11
EP0011598A1 (de)	1980-05-28
IL58375A0 (en)	1980-01-31
IE48698B1 (en)	1985-04-17
YU271679A (en)	1983-02-28
NO152784B (no)	1985-08-12
AU5109779A (en)	1980-05-22
IL58375A (en)	1984-02-29
NO793518L (no)	1980-05-19
AU525210B2 (en)	1982-10-28
FI793273A7 (fi)	1981-01-01
US4256764A (en)	1981-03-17
CS209828B2 (en)	1981-12-31
DK478979A (da)	1980-05-16
DE2964628D1 (en)	1983-03-03
ATA815178A (de)	1982-11-15
IE791863L (en)	1980-05-15
CA1141392A (en)	1983-02-15
ES8100285A1 (es)	1980-11-01
NO152784C (no)	1985-11-20
AT371453B (de)	1983-06-27
HU180037B (en)	1983-01-28
PT70455A (de)	1979-12-01
GR72529B (cs)	1983-11-17
ES485595A0 (es)	1980-11-01
NZ191718A (en)	1982-03-23
SU963466A3 (ru)	1982-09-30
ZA795022B (en)	1980-09-24
EP0011598B1 (de)	1983-01-26

Publication	Publication Date	Title
DE2708236A1 (de)	1977-09-08	3-aryl-2-oxazolidinone, verfahren zu ihrer herstellung und arzneimittel
EP0163260B1 (de)	1988-08-03	Neue substituierte Pyrrolidinone, Verfahren zu ihrer Herstellung und Arzneimittel
DE2847792C2 (cs)	1988-02-04
DE9290042U1 (de)	1993-12-16	Pro-Arzneimittelester von phenolischen 2-Piperidino-1-alkanolen
DE1957722A1 (de)	1971-05-19	Neue substituierte N-Aminoalkyl-arylaminoimidazoline-(2) und Verfahren zu deren Herstellung
DE1913199B2 (de)	1975-01-16	Mannichbasen aus alpha-Tetralon bzw. dessen Derivaten und Arylalkylaminen und deren Salze
DE3326724A1 (de)	1985-02-07	In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte
DD146951A5 (de)	1981-03-11	Verfahren zur herstellung von neuen derivaten von dimeren des isoeugenols
DE2658558A1 (de)	1978-06-29	Diazabicyclo(3,3,1)nonane, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2418142A1 (de)	1975-11-06	Tetracyclinderivate und verfahren zu ihrer herstellung
DE1545666A1 (de)	1969-06-26	Neue Diazacyloalkanverbindungen
AT390952B (de)	1990-07-25	Verfahren zur herstellung von neuen furan- oder thiophenderivaten
DE2410201C3 (de)	1978-08-10	6-Substituierte 3-Carbäthoxyhydrazinopyridazine beziehungsweise ihre Salze sowie solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben
EP0007438A1 (de)	1980-02-06	Neue substituierte 2-Phenylamino-imidazoline-(2), deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zur Herstellung derselben
DE2631080A1 (de)	1977-01-27	4-(3-substituierte-amino-2-hydroxy) propoxy-2-alkyl-isocarbostyril-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2314488A1 (de)	1974-10-03	Neue imidazo eckige klammer auf 1,2-a eckige klammer zu s-triazine, diese enthaltende arzneimittel, sowie verfahren zu deren herstellung
DD202025A5 (de)	1983-08-24	Verfahren zur herstellung von neuen n-substituierten polyglycidyl-urazolverbindungen
DE2831332A1 (de)	1979-02-08	Vinyloxyimino-derivate der 7-aminothiazolyl-acetamidocephalosporansaeure, ihre herstellung und pharmazeutische zusammensetzungen
DE3343884C2 (cs)	1991-07-11
EP0180889B1 (de)	1989-06-07	3-Amino-2,3-dihydro-1-benzoxepin-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
AT270657B (de)	1969-05-12	Verfahren zur Herstellung von neuen halogensubstituierten Tetrahydrochinazolinen sowie von deren Säureadditionssalzen
DE2951235A1 (de)	1980-11-06	Cyclododecanderivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel
DE1958212A1 (de)	1971-06-03	Neue substituierte N-Cycloalkyl-arylamino-imidazoline-(2) und Verfahren zu deren Herstellung
DE2720915A1 (de)	1978-11-23	Neue 1-acyl-2-hydroxy-1,3-diaminopropane, verfahren zur herstellung derselben und arzneimittel
AT352717B (de)	1979-10-10	Verfahren zur herstellung neuer 2,6-di- substituierter 2-phenylimino-imidazolidine und deren saeureadditionssalze