CH641437A5 - Cytostatisch-wirkende xylit-derivate. - Google Patents

Cytostatisch-wirkende xylit-derivate. Download PDF

Info

Publication number: CH641437A5
Authority: CH; Switzerland
Prior art keywords: xylitol; general formula; dianhydro; compounds; substituents
Prior art date: 1978-05-11

Application number

CH438979A

Other languages

German (de)

English (en)

Inventor

Ildiko Vidra-Sandor

Laszlo Institoris

Sandor Eckhardt

Karoly Lapis

Andras Jeney

Laszlo Kopper

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1978-05-11

Filing date

1979-05-10

Publication date

1984-02-29

1979-05-10 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1984-02-29 Publication of CH641437A5 publication Critical patent/CH641437A5/de

Links

HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 25
239000000811 xylitol Substances 0.000 claims description 23
229960002675 xylitol Drugs 0.000 claims description 23
-1 p-phenylbenzoyl Chemical group 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
239000011230 binding agent Substances 0.000 claims description 9
239000000825 pharmaceutical preparation Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
230000001085 cytostatic effect Effects 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000000824 cytostatic agent Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
229940083987 anhydroxylitol Drugs 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
239000012433 hydrogen halide Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
241001465754 Metazoa Species 0.000 description 17
239000000243 solution Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 10
241000699670 Mus sp. Species 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 5
239000003480 eluent Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000003708 ampul Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
FZQZRBQKXXGAMZ-UHFFFAOYSA-N 2-benzyl-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1CC1=CC=CC=C1 FZQZRBQKXXGAMZ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000002054 transplantation Methods 0.000 description 2
KZVAAIRBJJYZOW-VPENINKCSA-N (2r,3r,4s)-2-(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1OC[C@H](O)[C@H]1O KZVAAIRBJJYZOW-VPENINKCSA-N 0.000 description 1
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GSWQIGIUMPTMRX-VQFNDLOPSA-N C1(=CC=CC=C1)C1=CC=C(C(=O)[C@]([C@H](CBr)O)(O)[C@H](O)CBr)C=C1 Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)[C@]([C@H](CBr)O)(O)[C@H](O)CBr)C=C1 GSWQIGIUMPTMRX-VQFNDLOPSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229960004977 anhydrous lactose Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 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
238000007912 intraperitoneal administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/42—Polyhydroxylic acyclic alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Epoxy Compounds (AREA)

CH438979A 1978-05-11 1979-05-10 Cytostatisch-wirkende xylit-derivate. CH641437A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78CI1826A HU176216B (en)	1978-05-11	1978-05-11	Process for producing terminally bifuntional xylite derivatives of citostatic activity

Publications (1)

Publication Number	Publication Date
CH641437A5 true CH641437A5 (de)	1984-02-29

Family

ID=10994695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH438979A CH641437A5 (de)	1978-05-11	1979-05-10	Cytostatisch-wirkende xylit-derivate.

Country Status (26)

Country	Link
JP (1)	JPS5522662A (cs)
AR (1)	AR222332A1 (cs)
AT (1)	AT361945B (cs)
BE (1)	BE876166A (cs)
CA (1)	CA1145349A (cs)
CH (1)	CH641437A5 (cs)
CS (1)	CS211399B2 (cs)
DD (1)	DD143765A5 (cs)
DE (1)	DE2917538A1 (cs)
DK (1)	DK195279A (cs)
EG (1)	EG15150A (cs)
ES (1)	ES480869A1 (cs)
FI (1)	FI67845C (cs)
FR (1)	FR2425445A1 (cs)
GB (1)	GB2024204B (cs)
GR (1)	GR68495B (cs)
HU (1)	HU176216B (cs)
IL (1)	IL57182A (cs)
IN (1)	IN150040B (cs)
IT (1)	IT1118485B (cs)
NL (1)	NL7903634A (cs)
NO (1)	NO153928C (cs)
PL (1)	PL121560B1 (cs)
SE (1)	SE7904080L (cs)
SU (1)	SU984410A3 (cs)
YU (1)	YU108079A (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH381666A (de) *	1958-04-24	1964-09-15	Nat Res Dev	Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen
DE1668241A1 (de) *	1968-03-06	1971-02-11	Herbrand Kg Dr	Therapeutisch wirksame 1,5-di-substituierte Derivate von Xylit,Adonit und Arabit

1978
- 1978-05-11 HU HU78CI1826A patent/HU176216B/hu unknown
1979
- 1979-04-30 DE DE19792917538 patent/DE2917538A1/de not_active Withdrawn
- 1979-04-30 IL IL57182A patent/IL57182A/xx unknown
- 1979-05-02 IN IN447/CAL/79A patent/IN150040B/en unknown
- 1979-05-06 EG EG264/79A patent/EG15150A/xx active
- 1979-05-07 GR GR59037A patent/GR68495B/el unknown
- 1979-05-09 YU YU01080/79A patent/YU108079A/xx unknown
- 1979-05-09 FR FR7911733A patent/FR2425445A1/fr active Granted
- 1979-05-09 SE SE7904080A patent/SE7904080L/xx not_active Application Discontinuation
- 1979-05-09 FI FI791484A patent/FI67845C/fi not_active IP Right Cessation
- 1979-05-09 NL NL7903634A patent/NL7903634A/xx not_active Application Discontinuation
- 1979-05-10 AT AT347779A patent/AT361945B/de not_active IP Right Cessation
- 1979-05-10 NO NO791564A patent/NO153928C/no unknown
- 1979-05-10 CS CS793205A patent/CS211399B2/cs unknown
- 1979-05-10 GB GB7916274A patent/GB2024204B/en not_active Expired
- 1979-05-10 PL PL1979215489A patent/PL121560B1/pl unknown
- 1979-05-10 AR AR276464A patent/AR222332A1/es active
- 1979-05-10 IT IT67984/79A patent/IT1118485B/it active
- 1979-05-10 CA CA000327317A patent/CA1145349A/en not_active Expired
- 1979-05-10 DK DK195279A patent/DK195279A/da not_active Application Discontinuation
- 1979-05-10 CH CH438979A patent/CH641437A5/de not_active IP Right Cessation
- 1979-05-10 BE BE0/195089A patent/BE876166A/xx not_active IP Right Cessation
- 1979-05-10 JP JP5758879A patent/JPS5522662A/ja active Pending
- 1979-05-11 ES ES480869A patent/ES480869A1/es not_active Expired
- 1979-05-11 SU SU792764801A patent/SU984410A3/ru active
- 1979-05-11 DD DD79212780A patent/DD143765A5/de unknown

Also Published As

Publication number	Publication date
BE876166A (fr)	1979-09-03
PL121560B1 (en)	1982-05-31
PL215489A1 (cs)	1980-02-11
ATA347779A (de)	1980-09-15
DD143765A5 (de)	1980-09-10
IT7967984A0 (it)	1979-05-10
SU984410A3 (ru)	1982-12-23
AT361945B (de)	1981-04-10
ES480869A1 (es)	1980-06-16
FI67845C (fi)	1985-06-10
EG15150A (en)	1985-12-31
DE2917538A1 (de)	1979-11-15
GB2024204A (en)	1980-01-09
CS211399B2 (en)	1982-02-26
DK195279A (da)	1979-11-12
NO791564L (no)	1979-11-13
NO153928C (no)	1986-06-18
FR2425445A1 (fr)	1979-12-07
IL57182A0 (en)	1979-07-25
AR222332A1 (es)	1981-05-15
HU176216B (en)	1981-01-28
FI791484A7 (fi)	1979-11-12
NL7903634A (nl)	1979-11-13
FR2425445B1 (cs)	1984-06-08
GB2024204B (en)	1982-10-27
NO153928B (no)	1986-03-10
IT1118485B (it)	1986-03-03
IL57182A (en)	1983-07-31
SE7904080L (sv)	1979-11-12
YU108079A (en)	1982-10-31
FI67845B (fi)	1985-02-28
GR68495B (cs)	1982-01-07
JPS5522662A (en)	1980-02-18
CA1145349A (en)	1983-04-26
IN150040B (cs)	1982-07-03

Legal Events

Date	Code	Title	Description
1988-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
WO1980000152A1 (fr)	1980-02-07	Derives d'un 3-aminopropoxy-aryle, leur preparation et utilisation
EP0135762B1 (de)	1988-10-12	Steroide
DE2537070C2 (cs)	1987-06-25
DE2632400C2 (cs)	1988-06-09
EP0087655A1 (de)	1983-09-07	Verfahren zur Herstellung von Acemetacin
CH643830A5 (de)	1984-06-29	Bis-moranolin-derivate.
EP0103142A1 (de)	1984-03-21	Thieno(2,3-e)-1,2-thiazin-Derivate
DE2437147C2 (de)	1983-03-03	Phosphin- und Phosphit-Goldkomplexe und ihre Verwendung
EP0033919B1 (de)	1983-05-25	Substituierte Phosphin- und Phosphonsäuren, Verfahren und Zwischenprodukte zu ihrer Herstellung, diese enthaltende Arzneimittel und deren therapeutische Verwendung
CH641437A5 (de)	1984-02-29	Cytostatisch-wirkende xylit-derivate.
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