CH677668A5 - - Google Patents

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Info

Publication number: CH677668A5
Authority: CH; Switzerland
Prior art keywords: hydrogen; formula; compounds; independently; another
Prior art date: 1986-11-21

Application number

CH4410/87A

Other languages

German (de)

English (en)

Inventor

Cyril Dr Mahaim

Christos Dr Papageorgiou

Trevor James Dr Petcher

Original Assignee

Sandoz Ag

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.)

1986-11-21

Filing date

1987-11-12

Publication date

1991-06-14

1987-11-12 Application filed by Sandoz Ag filed Critical Sandoz Ag

1991-06-14 Publication of CH677668A5 publication Critical patent/CH677668A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 84
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 55
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
102000003946 Prolactin Human genes 0.000 claims description 12
108010057464 Prolactin Proteins 0.000 claims description 12
229940097325 prolactin Drugs 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
-1 3-dimethylaminopropyl Chemical group 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 8
230000028327 secretion Effects 0.000 claims description 8
239000004202 carbamide Substances 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
239000003112 inhibitor Substances 0.000 claims description 5
229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 4
238000005661 deetherification reaction Methods 0.000 claims description 4
150000003248 quinolines Chemical class 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
230000001263 anti-prolactin effect Effects 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000001718 carbodiimides Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000003291 dopaminomimetic effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
206010058359 Hypogonadism Diseases 0.000 description 1
208000019255 Menstrual disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
150000007945 N-acyl ureas Chemical class 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
206010036832 Prolactinoma Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
229960002802 bromocriptine Drugs 0.000 description 1
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000006651 lactation Effects 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
239000000155 melt Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH4410/87A 1986-11-21 1987-11-12 CH677668A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3639855		1986-11-21

Publications (1)

Publication Number	Publication Date
CH677668A5 true CH677668A5 (fr)	1991-06-14

Family

ID=6314490

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4410/87A CH677668A5 (fr)	1986-11-21	1987-11-12

Country Status (22)

Country	Link
JP (1)	JPS63150264A (fr)
KR (1)	KR880006200A (fr)
AT (1)	AT393836B (fr)
AU (1)	AU604512B2 (fr)
BE (1)	BE1003219A3 (fr)
CH (1)	CH677668A5 (fr)
DK (1)	DK608787A (fr)
ES (1)	ES2011309A6 (fr)
FI (1)	FI875130A7 (fr)
FR (1)	FR2607134A1 (fr)
GB (1)	GB2198129B (fr)
GR (1)	GR871777B (fr)
HU (1)	HUT47914A (fr)
IL (1)	IL84538A (fr)
IT (1)	IT1211920B (fr)
LU (1)	LU87047A1 (fr)
NL (1)	NL8702680A (fr)
NZ (1)	NZ222612A (fr)
PH (1)	PH25125A (fr)
PT (1)	PT86178B (fr)
SE (1)	SE8704551L (fr)
ZA (1)	ZA878717B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3879789A (en) *	1988-07-22	1990-02-19	Sandoz Ag	Use of benzo(g)quinolines in treatment of nicotine addiction
TW357143B (en) *	1995-07-07	1999-05-01	Novartis Ag	Benzo[g]quinoline derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526892A (en) *	1981-03-03	1985-07-02	Farmitalia Carlo Erba, S.P.A.	Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas
DE19575006I2 (de) *	1981-10-16	2003-01-09	Novartis Ag	1, 2, 3, 4a, 5, 10, 10a-Octahydrobenzo(g)chinolin-Derivate mit pharmazeutischer Wirkung
GB8602372D0 (en) *	1986-01-31	1986-03-05	Sandoz Ltd	Organic compounds

1987
- 1987-11-10 NL NL8702680A patent/NL8702680A/nl not_active Application Discontinuation
- 1987-11-12 CH CH4410/87A patent/CH677668A5/de not_active IP Right Cessation
- 1987-11-13 HU HU875063A patent/HUT47914A/hu unknown
- 1987-11-16 BE BE8701295A patent/BE1003219A3/fr not_active IP Right Cessation
- 1987-11-16 FR FR8715917A patent/FR2607134A1/fr not_active Withdrawn
- 1987-11-18 LU LU87047A patent/LU87047A1/fr unknown
- 1987-11-18 IT IT8748620A patent/IT1211920B/it active
- 1987-11-19 PT PT86178A patent/PT86178B/pt not_active IP Right Cessation
- 1987-11-19 DK DK608787A patent/DK608787A/da not_active Application Discontinuation
- 1987-11-19 GB GB8727057A patent/GB2198129B/en not_active Expired - Lifetime
- 1987-11-19 IL IL84538A patent/IL84538A/xx unknown
- 1987-11-19 FI FI875130A patent/FI875130A7/fi not_active IP Right Cessation
- 1987-11-19 NZ NZ222612A patent/NZ222612A/xx unknown
- 1987-11-19 AU AU81409/87A patent/AU604512B2/en not_active Ceased
- 1987-11-19 SE SE8704551A patent/SE8704551L/xx not_active Application Discontinuation
- 1987-11-20 AT AT0306187A patent/AT393836B/de not_active IP Right Cessation
- 1987-11-20 PH PH36098A patent/PH25125A/en unknown
- 1987-11-20 GR GR871777A patent/GR871777B/el unknown
- 1987-11-20 KR KR870013071A patent/KR880006200A/ko not_active Withdrawn
- 1987-11-20 ES ES8703316A patent/ES2011309A6/es not_active Expired - Lifetime
- 1987-11-20 ZA ZA878717A patent/ZA878717B/xx unknown
- 1987-11-20 JP JP62294995A patent/JPS63150264A/ja active Pending

Also Published As

Publication number	Publication date
FR2607134A1 (fr)	1988-05-27
GB2198129A (en)	1988-06-08
NL8702680A (nl)	1988-06-16
IL84538A (en)	1991-12-12
KR880006200A (ko)	1988-07-22
SE8704551L (sv)	1988-05-22
PT86178A (en)	1987-12-01
DK608787D0 (da)	1987-11-19
JPS63150264A (ja)	1988-06-22
HUT47914A (en)	1989-04-28
IT1211920B (it)	1989-11-08
FI875130A0 (fi)	1987-11-19
AU8140987A (en)	1988-05-26
AU604512B2 (en)	1990-12-20
IL84538A0 (en)	1988-04-29
SE8704551D0 (sv)	1987-11-19
DK608787A (da)	1988-05-22
GB8727057D0 (en)	1987-12-23
LU87047A1 (fr)	1988-06-13
GR871777B (en)	1988-03-24
AT393836B (de)	1991-12-27
FI875130A7 (fi)	1988-05-22
IT8748620A0 (it)	1987-11-18
ES2011309A6 (es)	1990-01-01
ATA306187A (de)	1991-06-15
ZA878717B (en)	1989-06-28
BE1003219A3 (fr)	1992-02-04
GB2198129B (en)	1990-08-08
NZ222612A (en)	1991-07-26
PT86178B (pt)	1990-11-07
PH25125A (en)	1991-02-19

Legal Events

Date	Code	Title	Description
1992-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69229339T2 (de)	1999-12-30	Kristallines tiagabinehydrochlorid-monohydrat, seine herstellung und verwendung
EP0153277A2 (fr)	1985-08-28	Dérivés de pleuromutiline, leur procédé de préparation et leur application
DE2615406A1 (de)	1976-10-14	Beta-adrenergische rezeptoren-blocker
DE2851435A1 (de)	1979-06-13	Substituierte amid-derivate des l- und dl-phenylglycins, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel
DD153372A5 (de)	1982-01-06	Verfahren zur herstellung von neuen ergolinderivaten
DE1795022C3 (de)	1981-06-19	Lysergsäurederivate
DE2524054A1 (de)	1975-12-18	1-cycloalkylmethyl-3a-(substituiertes-phenyl)-decahydroisochinoline
DE60131416T2 (de)	2008-09-18	Chirale fluochinolon-argininsalzformen
DE2524053A1 (de)	1975-12-18	1-aethyl-3a-substituiertes-phenyl- decahydroisochinoline
EP0155903B1 (fr)	1989-08-23	Indolophénanthridines, leur préparation et leur utilisation
EP0018360B1 (fr)	1981-09-30	N-(5-méthoxybenzofuran-2-ylcarbonyl)-N'-benzylpipérazine et procédé pour sa préparation
DE4131584A1 (de)	1993-03-25	Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika
EP0030380A1 (fr)	1981-06-17	Dérivés d'indoldione-2,3, procédé pour leur préparation, intermédiaires, médicaments contenant de tels dérivés de l'indoldione-2,3 et leur utilisation pharmaceutique
AT393836B (de)	1991-12-27	Neue octahydrobenzo(g)chinoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
CH617197A5 (fr)	1980-05-14
DD205682A5 (de)	1984-01-04	Verfahren zur herstellung von (-)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en und seinen salzen
DE2717001A1 (de)	1978-10-19	Arzneimittel mit antithrombotischer wirkung
DD232489A1 (de)	1986-01-29	Verfahren zur herstellung von s(-)-3-(3-acetyl-4-(3-tert. butylamino-2-hydroxypropoxy)-phenyl)-1,1-diaethylharnstoff
DE2357849A1 (de)	1974-06-06	Propanolaminderivate und arzneipraeparate
DE3738577A1 (de)	1988-07-28	Neue benzo(g)chinoline
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