DD231349A5 - Verfahren zur herstellung von oxysalicylsaeureamiden - Google Patents

Verfahren zur herstellung von oxysalicylsaeureamiden Download PDF

Info

Publication number: DD231349A5
Authority: DD; German Democratic Republic
Prior art keywords: group; compound; general formula; formula; groups
Prior art date: 1984-01-31

Application number

DD85272829A

Other languages

German (de)

English (en)

Inventor

Karl St Bengtsson

Thomas Hoegberg

Lars G Johansson

Tomas De Paulis

Hans E Peter

Marianne E Widman

Sven O Oegren

Original Assignee

��@��@��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.)

1984-01-31

Filing date

1985-01-29

Publication date

1985-12-24

1985-01-29 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1985-12-24 Publication of DD231349A5 publication Critical patent/DD231349A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 19
230000008569 process Effects 0.000 title claims description 4
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150000001875 compounds Chemical class 0.000 claims abstract description 124
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
-1 methylenedioxy Chemical group 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 26
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000002252 acyl group Chemical group 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims abstract description 8
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230000003287 optical effect Effects 0.000 claims abstract description 5
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238000012377 drug delivery Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000007938 effervescent tablet Substances 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
CMKFMAOMSNBJHX-MRXNPFEDSA-N n-[[(2r)-1-benzylpyrrolidin-2-yl]methyl]-3-bromo-2,5,6-trimethoxybenzamide Chemical compound COC1=CC(Br)=C(OC)C(C(=O)NC[C@@H]2N(CCC2)CC=2C=CC=CC=2)=C1OC CMKFMAOMSNBJHX-MRXNPFEDSA-N 0.000 description 1
PQQXQOJIDLXQOC-HNNXBMFYSA-N n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2,3,6-trimethoxy-5-propylbenzamide Chemical compound CCCC1=CC(OC)=C(OC)C(C(=O)NC[C@H]2N(CCC2)CC)=C1OC PQQXQOJIDLXQOC-HNNXBMFYSA-N 0.000 description 1
UQUSHEDVYVRCJT-LBPRGKRZSA-N n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2-hydroxy-5,6-dimethoxy-3-methylbenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(C)=CC(OC)=C1OC UQUSHEDVYVRCJT-LBPRGKRZSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical class NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
SIXNTGDWLSRMIC-UHFFFAOYSA-N sodium;toluene Chemical compound [Na].CC1=CC=CC=C1 SIXNTGDWLSRMIC-UHFFFAOYSA-N 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000002966 varnish Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD85272829A 1984-01-31 1985-01-29 Verfahren zur herstellung von oxysalicylsaeureamiden DD231349A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8400478A SE8400478D0 (sv)	1984-01-31	1984-01-31	Oxysalicylamido derivatives

Publications (1)

Publication Number	Publication Date
DD231349A5 true DD231349A5 (de)	1985-12-24

Family

ID=20354529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85272829A DD231349A5 (de)	1984-01-31	1985-01-29	Verfahren zur herstellung von oxysalicylsaeureamiden

Country Status (25)

Country	Link
EP (1)	EP0156776B1 (da)
JP (1)	JPH07103097B2 (da)
AT (1)	ATE41770T1 (da)
AU (1)	AU575113B2 (da)
CA (1)	CA1253869A (da)
CY (1)	CY1544A (da)
DD (1)	DD231349A5 (da)
DE (1)	DE3569111D1 (da)
DK (1)	DK38685A (da)
ES (3)	ES8609239A1 (da)
FI (1)	FI83771C (da)
GB (1)	GB2153354B (da)
GR (1)	GR850268B (da)
HK (1)	HK53090A (da)
HU (1)	HU198684B (da)
IE (1)	IE57888B1 (da)
IS (1)	IS1442B6 (da)
MY (1)	MY102377A (da)
NO (1)	NO171363C (da)
NZ (1)	NZ210939A (da)
PH (2)	PH22430A (da)
PT (1)	PT79900B (da)
SE (1)	SE8400478D0 (da)
SG (1)	SG35290G (da)
ZA (1)	ZA85158B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5446147A (en) *	1992-04-03	1995-08-29	Trustees Of The University Of Pennsylvania	Fluorinated and iodinated dopamine agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5822110B2 (ja) *	1977-08-08	1983-05-06	塩野義製薬株式会社	ベンズアミド誘導体の合成法
FR2440946A2 (fr) *	1978-01-20	1980-06-06	Ile De France	Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement
SE411118B (sv) *	1978-03-23	1979-12-03	Astra Laekemedel Ab	Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper
JPS55130957A (en) *	1979-03-30	1980-10-11	Kyowa Hakko Kogyo Co Ltd	Production of benzamide derivative
SE8101536L (sv) *	1981-03-11	1982-09-12	Astra Laekemedel Ab	Bensamid-derivat
SE8205135D0 (sv) *	1982-09-09	1982-09-09	Astra Laekemedel Ab	Benzamido-derivatives

1984
- 1984-01-31 SE SE8400478A patent/SE8400478D0/xx unknown
1985
- 1985-01-07 ZA ZA85158A patent/ZA85158B/xx unknown
- 1985-01-21 DE DE8585850022T patent/DE3569111D1/de not_active Expired
- 1985-01-21 NO NO850244A patent/NO171363C/no unknown
- 1985-01-21 EP EP85850022A patent/EP0156776B1/en not_active Expired
- 1985-01-21 AT AT85850022T patent/ATE41770T1/de not_active IP Right Cessation
- 1985-01-23 CA CA000472638A patent/CA1253869A/en not_active Expired
- 1985-01-25 AU AU38088/85A patent/AU575113B2/en not_active Ceased
- 1985-01-25 NZ NZ210939A patent/NZ210939A/xx unknown
- 1985-01-28 GB GB08502095A patent/GB2153354B/en not_active Expired
- 1985-01-28 PH PH31786A patent/PH22430A/en unknown
- 1985-01-29 DD DD85272829A patent/DD231349A5/de not_active IP Right Cessation
- 1985-01-29 DK DK38685A patent/DK38685A/da not_active Application Discontinuation
- 1985-01-30 HU HU85343A patent/HU198684B/hu not_active IP Right Cessation
- 1985-01-30 IE IE220/85A patent/IE57888B1/en not_active IP Right Cessation
- 1985-01-30 FI FI850398A patent/FI83771C/fi not_active IP Right Cessation
- 1985-01-30 PT PT79900A patent/PT79900B/pt not_active IP Right Cessation
- 1985-01-30 ES ES539955A patent/ES8609239A1/es not_active Expired
- 1985-01-30 JP JP60014622A patent/JPH07103097B2/ja not_active Expired - Lifetime
- 1985-01-30 GR GR850268A patent/GR850268B/el unknown
- 1985-01-31 IS IS2974A patent/IS1442B6/is unknown
1986
- 1986-01-13 ES ES550826A patent/ES8801199A1/es not_active Expired
- 1986-01-13 ES ES550825A patent/ES8707712A1/es not_active Expired
1987
- 1987-09-29 MY MYPI87002193A patent/MY102377A/en unknown
1988
- 1988-02-29 PH PH36568A patent/PH24046A/en unknown
1990
- 1990-05-18 SG SG352/90A patent/SG35290G/en unknown
- 1990-07-12 HK HK530/90A patent/HK53090A/xx not_active IP Right Cessation
1991
- 1991-03-22 CY CY1544A patent/CY1544A/en unknown

Also Published As

Publication number	Publication date
NO171363B (no)	1992-11-23
SE8400478D0 (sv)	1984-01-31
IE850220L (en)	1985-07-31
JPH07103097B2 (ja)	1995-11-08
FI83771C (fi)	1991-08-26
ATE41770T1 (de)	1989-04-15
ES539955A0 (es)	1986-09-01
CY1544A (en)	1991-03-22
PT79900A (en)	1985-02-01
NO171363C (no)	1993-03-03
AU3808885A (en)	1985-08-08
HU198684B (en)	1989-11-28
IS1442B6 (is)	1990-12-14
JPS60178859A (ja)	1985-09-12
HUT37750A (en)	1986-02-28
ES8609239A1 (es)	1986-09-01
SG35290G (en)	1990-07-13
EP0156776A1 (en)	1985-10-02
ES550825A0 (es)	1987-08-16
NO850244L (no)	1985-08-01
EP0156776B1 (en)	1989-03-29
GR850268B (da)	1985-05-28
DK38685D0 (da)	1985-01-29
FI850398L (fi)	1985-08-01
HK53090A (en)	1990-07-20
FI850398A0 (fi)	1985-01-30
GB2153354A (en)	1985-08-21
ES8707712A1 (es)	1987-08-16
PH22430A (en)	1988-09-12
FI83771B (fi)	1991-05-15
ES8801199A1 (es)	1987-12-16
MY102377A (en)	1992-06-17
IE57888B1 (en)	1993-05-05
AU575113B2 (en)	1988-07-21
PT79900B (en)	1987-02-03
GB2153354B (en)	1987-10-21
DK38685A (da)	1985-08-01
NZ210939A (en)	1988-10-28
CA1253869A (en)	1989-05-09
GB8502095D0 (en)	1985-02-27
IS2974A7 (is)	1985-08-01
PH24046A (en)	1990-03-05
DE3569111D1 (en)	1989-05-03
ES550826A0 (es)	1987-12-16
ZA85158B (en)	1985-09-25

Legal Events

Date	Code	Title	Description
2000-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0261539B1 (de)	1991-03-06	Substituierte Phenylsulfonamide
DE69613240T2 (de)	2002-04-25	N-aminoalkylfluorencarboxamide, neue klasse von dopaminerezeptor subtype spezifische liganden
DE60102581T2 (de)	2005-02-03	Azabizyklische carbamate und ihre anwendung als antagonisten des alpha-7 nikotinischen acetylcholin rezeptors
DE2901032C2 (de)	1996-05-30	Substituierte Morpholin-Derivate und deren Verwendung
DE69332559T2 (de)	2003-11-20	2,3,4,5-tetrahydro-1h-3-benzazepinen mit anti-psychotisch wirkung, und synthese von alfa-substituierten-arylacetamiden
EP1694318B1 (de)	2007-03-14	(s)-2-n-propylamino-5-hydroxytetralin als d3-agonistisches therapeutikum
DE69330926T2 (de)	2002-04-11	Isoxazolderivate zur Behandlung von Darmreizungssyndromen
DE69724422T2 (de)	2004-03-11	Arylalkylpiperazin-verbindungen als antioxidantien
DE69501596T2 (de)	1998-09-10	Derivate des N-(3-Aminopropyl)-N-phenyl-5,6,7,8-tetrahydronaphthalen-2-carboxamides mit neuroprotektiven und antischaemischen Eigenschaften, ihre Herstellung und ihre therapeutische Verwendung
DE69417235T2 (de)	1999-07-08	IMIDAZO[1,2-a]PYRAZIN-4-ON-DERIVATE ANTAGONISTEN DER AMPA UND NMDA REZEPTOREN
DE69120899T2 (de)	1997-02-27	Neue N-Benzoylprolin-Derivate, Verfahren zur Herstellung und diese enthaltende Arzneimittel
EP0177960B1 (de)	1991-03-20	Tetrahydronaphtalinderivate, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende Arzneimittel
DD201886A5 (de)	1983-08-17	Verfahren zur herstellung von benzamidoverbindungen
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