EP0000825B1 - Dérivés de l'indène à deux substituants géminaux, leurs procédés de préparation et compositions pharmaceutiques les contenant - Google Patents

Dérivés de l'indène à deux substituants géminaux, leurs procédés de préparation et compositions pharmaceutiques les contenant Download PDF

Info

Publication number
EP0000825B1
EP0000825B1 EP78300226A EP78300226A EP0000825B1 EP 0000825 B1 EP0000825 B1 EP 0000825B1 EP 78300226 A EP78300226 A EP 78300226A EP 78300226 A EP78300226 A EP 78300226A EP 0000825 B1 EP0000825 B1 EP 0000825B1
Authority
EP
European Patent Office
Prior art keywords
compound
formula
indene
group
cyclopentane
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
EP78300226A
Other languages
German (de)
English (en)
Other versions
EP0000825A1 (fr
Inventor
Aake Nils Joensson
Tomas Goeran Kempe
Lembit Mikiver
Bengt Aake Sparf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Phadia AB
Original Assignee
Kabi AB
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.)
Filing date
Publication date
Application filed by Kabi AB filed Critical Kabi AB
Publication of EP0000825A1 publication Critical patent/EP0000825A1/fr
Application granted granted Critical
Publication of EP0000825B1 publication Critical patent/EP0000825B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C07C215/38—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings with rings other than six-membered aromatic rings being part of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/453—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms

Landscapes

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

Claims (19)

1. Indènes géminalement disubstitués, caractérisés en ce qu'ils répondent à la formule générale (I) suivante:
Figure imgb0038
dans laquelle chacun des substituants R1 et R2 est de l'hydrogène, ou bien R1 et R2 établissent et représentent une liaison directe ou un radical alcoylène -(CH2)n- où n est un nombre entier de 1 à 4; R3 est hydrogène, un radical alcoxy comportant de 1 à 3 atomes de carbone, ou halogène; et chacun des substituants R4 et R5 est de l'hydrogène, ou bien alcoyle inférieur comportant de 1 à 4 atomes de carbone, ou bien encore R4 et R5 constituent conjointement un radical alcoylène -(CH2)m- où m est un nombre entier de 3 à 6; ainsi que les dérivés correspondants de tels indènes, dérivés des types oxydes d'amine, composés d'ammonium quaternaires et sels avec des acides physiologiquement acceptables.
2. Indène selon la revendication 1, caractérisé en ce que R1 et R2 constituent conjointement un radical -CH2-CH2- ou -(CH2)3-, ou bien chacun de ces substituants R1 et R2 représente de l'hydrogène.
3. Indène selon la revendication 1 ou 2, caractérisé en ce que R4 est H, et R5 est H ou CH3.
4. Le 2-amino-1-[spiro(cyclopentane-1,1'-indène)-3'-yl]-éthanol.
5. Le 2-méthylamino-1-[spiro-(cyclopentane-1,1'-indène)-3'-yl]-éthanol.
6. Le 2-amino-1-[1,1-diméthylindène-3-yl]-éthanol.
7. Indène selon l'une quelconque des revendications 2 à 6, caractérisé en ce qu'il se présente sous la forme de l'un des sels suivants: chlorhydrate, hydrogénofumarate, hydrogénooxalate, hydro- génotartrate.
8. Indène selon l'une quelconque des revendications 1 à 7, caractérisé en ce qu'il se présente sous la forme d'un isomère optiquement actif.
9. Procédé de préparation d'un composé répondant à la formule générale (I), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend la réaction d'un composé répondant à la formule générale (II) suivante:
Figure imgb0039
avec une amine de formule NHR4R5, où le terme "Cycle" représente le groupe:
Figure imgb0040
dans laquel R1, R2, R3, R4 et R5 sont tels que définis dans la revendication 1, et X est un groupe ou radical détachable, doté de réactivité.
10. Procédé de préparation d'un composé répondant à la formule (I), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend la réaction d'un composé de formule générale (IV) suivante:
Figure imgb0041
dans laquelle le terme "Cycle" est tel que défini dans la revendication 9, et Z est le radical aminométhyle -CH2-N(R4)R5 ou un radical convertible en un tel radical aminométhyle dans des conditions qui permettent la réduction du radical CO en CH(OH); et R4 et R5 sont tels que définis dans la revendication 1.
11. Procédé de préparation d'un composé de formule générale (1), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend la réduction d'un composé de formule générale (V) suivante:
Figure imgb0042
dans laquelle le terme "Cycle" est tel que défini dans la revendication 9, et Y est un radical réductible en un radical aminométhyle -CH2-N(R4)R5 où R4 et R5 sont tels que définis dans la revendication 1.
12. Procédé de préparation d'un composé de formule générale (1), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend l'oxydation d'un composé de formule générale (VI) suivante:
Figure imgb0043
afin de former un composé de formule générale (VII) ou (VIII):
Figure imgb0044
ledit composé de formule (VII) ou (VIII) étant ensuite soumis à une déshydratation ou à une transposition afin de former un composé de formule générale (I), les substituants R1, R2, R3, R4 et R5 étant tels que définis dans la revendication 1.
13. Procédé de préparation d'un composé de formule générale (I), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend la réaction d'un époxyde de formule générale (IX) suivante:
Figure imgb0045
avec une amine de formule générale HN(R4)R5, les substituants R1, R2, R3, R4 et R5 étant tels que définis dans la revendication 1.
14. Procédé de préparation d'un composé représentable par la formule générale (I), tel que défini dans la revendication 1, caractérisé en ce qu'il comprend l'élimination du radical ou groupe protecteur amino à partir d'un composé de formule générale (X) suivante:
Figure imgb0046
dans laquelle les substituants R1, R2 et R3 sont tels que définis dans la revendication 1, cependant que R4' et R5' sont identiques respectivement à R4 et R5 ou bien sont chacun un groupe protecteur, au moins l'un de ces derniers substituants représentant un tel groupe protecteur.
15. Procédé selon l'une quelconque des revendications 9 à 14, caractérisé en ce que l'on prépare une base libre, puis on la convertit en un sel quaternaire par réaction avec un agent de quaternisation, ou bien on la convertit en un sel d'addition avec un acide par réaction avec un acide pharmaceutique- ment acceptable.
16. Procédé selon l'une quelconque des revendications 9 à 15, caractérisé en ce que l'on oxyde l'amine en l'oxyde d'amine correspondant.
17. Procédé selon l'une quelconque des revendications 9 à 16, caractérisé en ce que l'on isole un isomère optiquement actif.
18. Composition pharmaceutique caractérisée en ce qu'elle comprend au moins un composé, sel, oxyde d'amine ou isomère optiquement actif d'une telle substance selon l'une quelconque des revendications 1 à 8, conjointement avec un diluant, support ou véhicule inerte.
19. Utilisation d'un composé, sel, oxyde d'amine ou isomère optiquement actif d'une telle substance selon l'une quelconque des revendications 1 à 8, pour le traitement d'une incontinence par stress, comme agent décongestionnant de membranes muqueuses, comme agent d'abaissement de la pression sanguine, comme agent vasoconstricteur, ou comme agent anti-réserpine.
EP78300226A 1977-08-05 1978-08-01 Dérivés de l'indène à deux substituants géminaux, leurs procédés de préparation et compositions pharmaceutiques les contenant Expired EP0000825B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3294777 1977-08-05
GB3294777 1977-08-05

Publications (2)

Publication Number Publication Date
EP0000825A1 EP0000825A1 (fr) 1979-02-21
EP0000825B1 true EP0000825B1 (fr) 1982-04-14

Family

ID=10346367

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78300226A Expired EP0000825B1 (fr) 1977-08-05 1978-08-01 Dérivés de l'indène à deux substituants géminaux, leurs procédés de préparation et compositions pharmaceutiques les contenant

Country Status (16)

Country Link
US (1) US4218472A (fr)
EP (1) EP0000825B1 (fr)
JP (1) JPS5444651A (fr)
AT (1) AT367018B (fr)
AU (1) AU527825B2 (fr)
CA (1) CA1109066A (fr)
DE (1) DE2861735D1 (fr)
DK (1) DK150538C (fr)
ES (1) ES472291A1 (fr)
FI (1) FI71724C (fr)
IE (1) IE47716B1 (fr)
IT (1) IT1099587B (fr)
NO (1) NO147420C (fr)
NZ (1) NZ188037A (fr)
PT (1) PT68383A (fr)
ZA (1) ZA784349B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4331549A (en) * 1980-04-21 1982-05-25 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of ketones
KR100595963B1 (ko) * 2004-04-13 2006-07-05 한국화학연구원 인덴 유도체 및 이의 제조방법
KR101959636B1 (ko) * 2017-10-25 2019-07-04 경북대학교 산학협력단 인데엔 화합물을 유효성분으로 함유하는 골 재생 및 골 질환 예방 또는 치료용 조성물

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE371190B (fr) * 1972-03-24 1974-11-11 Kabi Ab
US2532292A (en) * 1947-12-12 1950-12-05 Searle & Co Diarylmethyl ethers of amino alkanols
DE955594C (de) * 1953-11-15 1957-01-03 Schering Ag Verfahren zur Herstellung von 3-Aminoindanen
US2914561A (en) * 1957-08-06 1959-11-24 Wm S Merrell Co Amine derivatives of triphenylethylene
US2987442A (en) * 1959-02-17 1961-06-06 Smith Kline French Lab Method of treating hypertension with [2-(2, 6-dimethylphenoxy)-propyl]-trimethyl ammonium salts
US2971001A (en) * 1959-10-21 1961-02-07 Wm S Merrell Co Quaternary salts of triphenylethanols, -ethylenes, and -ethanes
US3205136A (en) * 1962-12-24 1965-09-07 Smith Kline French Lab Antidepressant phenyloxyalkylamines
US3255249A (en) * 1963-04-26 1966-06-07 Ici Ltd 2-branched lower alkyl-amino-1-(indan-, hydrogenated indan- and hydrogenated naphth-2-yl) lower alkanols
GB1059968A (en) * 1964-01-20 1967-02-22 Ici Ltd Naphthalene derivatives
US3532752A (en) * 1965-12-30 1970-10-06 Merck & Co Inc 1-alkylidene-3-indenyl aliphatic amines
GB1187255A (en) * 1966-12-01 1970-04-08 Mead Johnson & Co 0-(2-Dimethylaminoethyl)-1-Phenylindene-N-Oxide, Acid Addition Salts thereof, and Process for Preparing the same
CH540221A (de) * 1968-03-20 1973-08-15 Hoffmann La Roche Verfahren zur Herstellung von tricyclischen Verbindungen
US4136116A (en) * 1968-05-03 1979-01-23 Hoffmann-La Roche Inc. Tricyclic compounds
US4127675A (en) * 1968-11-12 1978-11-28 Yamanouchi Pharmaceutical Co., Ltd. 4-(Alkylamino-2-hydroxypropoxy)-indenes and method of use
US3940443A (en) * 1973-06-07 1976-02-24 The United States Of America As Represented By The Secretary Of The Navy Amino ethanol-indane and tetrahydronaphthalene derivatives
FR2363327A1 (fr) * 1976-08-31 1978-03-31 Continental Pharma Nouveaux amino-alcools heterocycliques, leurs sels et leur procede de preparation

Also Published As

Publication number Publication date
DE2861735D1 (en) 1982-05-27
JPS5444651A (en) 1979-04-09
PT68383A (en) 1978-09-01
DK344778A (da) 1979-02-06
AT367018B (de) 1982-05-25
IT7826404A0 (it) 1978-08-02
ZA784349B (en) 1979-07-25
NO147420B (no) 1982-12-27
CA1109066A (fr) 1981-09-15
DK150538C (da) 1987-10-12
AU3857878A (en) 1980-02-07
FI71724C (fi) 1987-02-09
EP0000825A1 (fr) 1979-02-21
NO147420C (no) 1983-04-06
NO782651L (no) 1979-02-06
ES472291A1 (es) 1979-02-16
DK150538B (da) 1987-03-23
ATA563378A (de) 1981-10-15
FI71724B (fi) 1986-10-31
FI782382A (fi) 1979-02-06
NZ188037A (en) 1984-07-06
AU527825B2 (en) 1983-03-24
IE47716B1 (en) 1984-05-30
IT1099587B (it) 1985-09-18
IE781561L (en) 1979-02-05
JPS6344737B2 (fr) 1988-09-06
US4218472A (en) 1980-08-19

Similar Documents

Publication Publication Date Title
CA1086317A (fr) Substances heterocycliques aminoalkylees
US4268673A (en) 5-Unsubstituted-9,9-dimethyl-6,7-benzomorphans
JP2637737B2 (ja) 新規な薬剤
JPH0261465B2 (fr)
LU86435A1 (fr) Nouveaux derives du morphinane et de la morphine,leur preparation,leur application comme medicaments et les compositions pharmaceutiques les contenant
US3804899A (en) 3-alkylamino-2-(3,4-dihydroxyphenyl)propanols and the salts thereof
EP0461986B1 (fr) Dérivés d'hexahydroazépines, un procédé pour leur préparation et compositions pharmaceutiques les contenant
EP1214313B1 (fr) Heteroaryloxypropanolamines comme agonistes du recepteur beta3-adrenergique
EP0000825B1 (fr) Dérivés de l'indène à deux substituants géminaux, leurs procédés de préparation et compositions pharmaceutiques les contenant
BE1009852A3 (fr) Derives 1-[2(vinyl-substitues)]-3-4-dihydro-5h-2,3-benzodiazepine.
GB1569251A (en) Pyridobenzodiazepines
EP0018417B1 (fr) Nouveaux derives de piperidine et compositions pharmaceutiques les contenant
EP0053964B1 (fr) Médicaments à base de dérivés de (quinolyl-4)-1 éthanol ou propanol, nouveaux dérivés de (quinolyl-4)-1 éthanol ou propanol et procédés pour leur préparation
US4272533A (en) N-Phenylindoline derivatives, and pharmaceutical compositions containing them
JPH0260653B2 (fr)
US3696121A (en) 4-(2-hydroxy-3-amino propoxy)-indole derivatives
US3894051A (en) N-methylenedioxyphenylalkyl)-{62 -(alkyl)-disubstituted phenethylamines
EP0139921B1 (fr) Dérivés de 2-phényléthylamine
EP0118489A1 (fr) Arylethanol amines secondaires
US4927819A (en) Cyclo-octane neuroprotective agents
US4252824A (en) Amino-ethanol derivatives
GB1594687A (en) 2-aminotetralin derivatives and processes for producing the same
JPS6123178B2 (fr)
US3988362A (en) Intermediates for preparation of 2,2,3-endotrimethyl-7-anti-amino-norbornanes
US4123545A (en) N-Propyl-3(β-hydroxyethyl)-3-(meta-hydroxyphenyl)-pyrrolidine

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE CH DE FR GB LU NL SE

17P Request for examination filed
DET De: translation of patent claims
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB LU NL SE

REF Corresponds to:

Ref document number: 2861735

Country of ref document: DE

Date of ref document: 19820527

KL Correction list

Free format text: 82/06

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19920721

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19920807

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19920814

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19920817

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19920824

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19920831

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 19920903

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19920918

Year of fee payment: 15

EPTA Lu: last paid annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19930801

Ref country code: GB

Effective date: 19930801

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19930802

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19930831

Ref country code: BE

Effective date: 19930831

BERE Be: lapsed

Owner name: KABI A.B.

Effective date: 19930831

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940301

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19930801

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19940429

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19940503

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

EUG Se: european patent has lapsed

Ref document number: 78300226.4

Effective date: 19940310

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT