IE57809B1 - 1,2,3,9-tetrahydro-3-(imidazol-1-ylmethyl)-4h-carbazol-4 one derivatives - Google Patents

1,2,3,9-tetrahydro-3-(imidazol-1-ylmethyl)-4h-carbazol-4 one derivatives

Info

Publication number: IE57809B1
Authority: IE; Ireland
Prior art keywords: methyl; compound; group; formula; physiologically acceptable
Prior art date: 1984-01-25

Application number

IE187/85A

Other languages

English (en)

Other versions

IE850187L (en

Original Assignee

Glaxo Group Ltd

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.)

1984-01-25

Filing date

1985-01-25

Publication date

1993-04-21

1984-01-25 Priority claimed from GB848401888A external-priority patent/GB8401888D0/en

1984-10-15 Priority claimed from GB848425959A external-priority patent/GB8425959D0/en

1985-01-25 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1985-07-25 Publication of IE850187L publication Critical patent/IE850187L/xx

1993-04-21 Publication of IE57809B1 publication Critical patent/IE57809B1/en

Links

150000001875 compounds Chemical class 0.000 claims abstract description 130
150000003839 salts Chemical class 0.000 claims abstract description 46
-1 hydrates Chemical class 0.000 claims abstract description 28
239000012453 solvate Substances 0.000 claims abstract description 19
125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 44
238000000034 method Methods 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
230000008569 process Effects 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
239000012458 free base Substances 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
238000005804 alkylation reaction Methods 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 claims description 3
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 2
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical class N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 11
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150000002431 hydrogen Chemical class 0.000 abstract 1
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239000002904 solvent Substances 0.000 description 17
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
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229910000104 sodium hydride Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 5
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125000004423 acyloxy group Chemical group 0.000 description 4
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WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
LLWRXQXPJMPHLR-UHFFFAOYSA-N methylazanium;iodide Chemical compound [I-].[NH3+]C LLWRXQXPJMPHLR-UHFFFAOYSA-N 0.000 description 1
TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
229960004503 metoclopramide Drugs 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
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
210000000578 peripheral nerve Anatomy 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
230000037047 psychomotor activity Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 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
150000003335 secondary amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
230000036578 sleeping time Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229940098466 sublingual tablet Drugs 0.000 description 1
229960004016 sucrose syrup Drugs 0.000 description 1
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IE187/85A 1984-01-25 1985-01-25 1,2,3,9-tetrahydro-3-(imidazol-1-ylmethyl)-4h-carbazol-4 one derivatives IE57809B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB848401888A GB8401888D0 (en)	1984-01-25	1984-01-25	Heterocyclic compounds
GB848425959A GB8425959D0 (en)	1984-10-15	1984-10-15	Heterocyclic compounds

Publications (2)

Publication Number	Publication Date
IE850187L IE850187L (en)	1985-07-25
IE57809B1 true IE57809B1 (en)	1993-04-21

Family

ID=26287221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE187/85A IE57809B1 (en)	1984-01-25	1985-01-25	1,2,3,9-tetrahydro-3-(imidazol-1-ylmethyl)-4h-carbazol-4 one derivatives

Country Status (29)

Country	Link
KR (1)	KR920003064B1 (fr)
AT (1)	AT392276B (fr)
AU (1)	AU579132B2 (fr)
BE (1)	BE901576A (fr)
CA (1)	CA1252793A (fr)
CH (1)	CH664152A5 (fr)
CY (1)	CY1479A (fr)
CZ (1)	CZ404391A3 (fr)
DE (2)	DE3502508A1 (fr)
DK (1)	DK169521B1 (fr)
ES (3)	ES8609309A1 (fr)
FI (1)	FI84349C (fr)
FR (1)	FR2561244B1 (fr)
GB (1)	GB2153821B (fr)
GR (1)	GR850219B (fr)
HK (1)	HK33189A (fr)
HU (1)	HU193592B (fr)
IE (1)	IE57809B1 (fr)
IL (1)	IL74165A (fr)
IT (1)	IT1182150B (fr)
LU (2)	LU88268I2 (fr)
NL (2)	NL190373C (fr)
NO (2)	NO164025C (fr)
NZ (1)	NZ210940A (fr)
PH (1)	PH22672A (fr)
PT (1)	PT79890B (fr)
SE (1)	SE460359B (fr)
SG (1)	SG7089G (fr)
SK (1)	SK277923B6 (fr)

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CN115611864A (zh) *	2022-11-01	2023-01-17	常州兰陵制药有限公司	一种昂丹司琼类化合物及其制备方法与应用
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US3634420A (en) *	1969-05-09	1972-01-11	American Cyanamid Co	3(morpholinomethyl)-2 3-dihydro-carbazol-4(1h)-ones
US3740404A (en) *	1969-05-09	1973-06-19	American Cyanamid Co	Piperidinomethylenedihydrocarbazolones
DE3680123D1 (en) *	1985-01-23	1991-08-14	Glaxo Group Ltd	Tetrahydrocarbazolonderivate.

1985
- 1985-01-25 NZ NZ210940A patent/NZ210940A/xx unknown
- 1985-01-25 BE BE0/214394A patent/BE901576A/fr not_active IP Right Cessation
- 1985-01-25 FR FR8501056A patent/FR2561244B1/fr not_active Expired
- 1985-01-25 DE DE19853502508 patent/DE3502508A1/de active Granted
- 1985-01-25 GR GR850219A patent/GR850219B/el active IP Right Revival
- 1985-01-25 AT AT204/85A patent/AT392276B/de not_active IP Right Cessation
- 1985-01-25 CH CH346/85A patent/CH664152A5/fr not_active IP Right Cessation
- 1985-01-25 LU LU88268C patent/LU88268I2/xx unknown
- 1985-01-25 DE DE1993175046 patent/DE19375046I2/de active Active
- 1985-01-25 CA CA000472888A patent/CA1252793A/fr not_active Expired
- 1985-01-25 FI FI850323A patent/FI84349C/fi not_active IP Right Cessation
- 1985-01-25 NL NLAANVRAGE8500202,A patent/NL190373C/xx not_active IP Right Cessation
- 1985-01-25 LU LU85743A patent/LU85743A1/fr active Protection Beyond IP Right Term
- 1985-01-25 IT IT47600/85A patent/IT1182150B/it active Protection Beyond IP Right Term
- 1985-01-25 IE IE187/85A patent/IE57809B1/en not_active IP Right Cessation
- 1985-01-25 NO NO850300A patent/NO164025C/no not_active IP Right Cessation
- 1985-01-25 DK DK035785A patent/DK169521B1/da not_active IP Right Cessation
- 1985-01-25 IL IL74165A patent/IL74165A/xx not_active IP Right Cessation
- 1985-01-25 PT PT79890A patent/PT79890B/pt unknown
- 1985-01-25 GB GB08501889A patent/GB2153821B/en not_active Expired
- 1985-01-25 PH PH31770A patent/PH22672A/en unknown
- 1985-01-25 HU HU85296A patent/HU193592B/hu unknown
- 1985-01-25 KR KR1019850000454A patent/KR920003064B1/ko not_active IP Right Cessation
- 1985-01-25 ES ES539852A patent/ES8609309A1/es not_active Expired
- 1985-01-25 AU AU38097/85A patent/AU579132B2/en not_active Expired
- 1985-01-25 SE SE8500368A patent/SE460359B/sv not_active IP Right Cessation
- 1985-10-31 ES ES548430A patent/ES8708224A1/es not_active Expired
1986
- 1986-06-16 ES ES556101A patent/ES8801247A1/es not_active Expired
1989
- 1989-02-09 SG SG70/89A patent/SG7089G/en unknown
- 1989-04-20 HK HK331/89A patent/HK33189A/xx not_active IP Right Cessation
- 1989-07-21 CY CY1479A patent/CY1479A/xx unknown
1991
- 1991-12-23 CZ CS914043A patent/CZ404391A3/cs unknown
- 1991-12-23 SK SK4043-91A patent/SK277923B6/sk unknown
1994
- 1994-05-31 NL NL940009C patent/NL940009I2/nl unknown
- 1994-11-09 NO NO1994022C patent/NO1994022I1/no unknown

Also Published As

Publication number	Publication date
AU3809785A (en)	1985-08-01
CH664152A5 (fr)	1988-02-15
HUT37784A (en)	1986-02-28
IT1182150B (it)	1987-09-30
LU85743A1 (fr)	1986-08-04
PH22672A (en)	1988-11-14
NZ210940A (en)	1989-08-29
ES8801247A1 (es)	1987-12-16
AU579132B2 (en)	1988-11-17
BE901576A (fr)	1985-07-25
FI84349C (fi)	1991-11-25
NL8500202A (nl)	1985-08-16
ES8708224A1 (es)	1987-10-01
GB8501889D0 (en)	1985-02-27
FR2561244B1 (fr)	1988-03-04
NL940009I2 (nl)	1999-05-03
NL940009I1 (nl)	1994-07-18
SE8500368L (sv)	1985-07-26
KR920003064B1 (ko)	1992-04-13
DE19375046I2 (de)	2002-10-10
SG7089G (en)	1989-06-09
SE8500368D0 (sv)	1985-01-25
ES539852A0 (es)	1986-07-16
GR850219B (fr)	1985-05-23
ES8609309A1 (es)	1986-07-16
FI850323L (fi)	1985-07-26
ATA20485A (de)	1990-08-15
NL190373B (nl)	1993-09-01
HK33189A (en)	1989-04-28
NO164025C (no)	1990-08-22
AT392276B (de)	1991-02-25
SK404391A3 (en)	1995-08-09
PT79890B (en)	1987-02-03
CY1479A (en)	1989-07-21
NO164025B (no)	1990-05-14
ES556101A0 (es)	1987-12-16
DE3502508A1 (de)	1985-08-14
SE460359B (sv)	1989-10-02
CZ404391A3 (en)	1993-04-14
SK277923B6 (en)	1995-08-09
DK169521B1 (da)	1994-11-21
IL74165A (en)	1988-11-15
DK35785A (da)	1985-07-26
ES548430A0 (es)	1987-10-01
DK35785D0 (da)	1985-01-25
FI850323A0 (fi)	1985-01-25
GB2153821A (en)	1985-08-29
NO850300L (no)	1985-07-26
FR2561244A1 (fr)	1985-09-20
CA1252793A (fr)	1989-04-18
GB2153821B (en)	1988-01-20
FI84349B (fi)	1991-08-15
PT79890A (en)	1985-02-01
NL190373C (nl)	1994-02-01
DE3502508C2 (fr)	1990-05-03
IE850187L (en)	1985-07-25
HU193592B (en)	1987-11-30
KR850005439A (ko)	1985-08-26
LU88268I2 (fr)	1994-02-03
IT8547600A0 (it)	1985-01-25
NO1994022I1 (no)	1994-11-09

Publication	Publication Date	Title
IE57809B1 (en)	1993-04-21	1,2,3,9-tetrahydro-3-(imidazol-1-ylmethyl)-4h-carbazol-4 one derivatives
US4695578A (en)	1987-09-22	1,2,3,9-tetrahydro-3-imidazol-1-ylmethyl-4H-carbazol-4-ones, composition containing them, and method of using them to treat neuronal 5HT function disturbances
EP0191562B1 (fr)	1991-07-10	Dérivés de tétrahydrocarbazolones
EP0210840B1 (fr)	1992-03-11	Imidazolylméthyltétrahydrocarbazolones substituées
BE1001004A4 (fr)	1989-06-06	Nouvelles cetones tricycliques utiles comme medicaments, procede et intermediaires pour leur preparation.
US4725615A (en)	1988-02-16	Carbazole derivatives and their use as 5HT-induced antagonists
AU613662B2 (en)	1991-08-08	Lactam derivatives
US5068234A (en)	1991-11-26	3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles
US5045545A (en)	1991-09-03	[(Imidazol-4(and 5)-yl)methyl] tetracyclic ketones having 5-HT3 antagonist activity
EP0266899A2 (fr)	1988-05-11	Dérivés d'indole
EP0339959A2 (fr)	1989-11-02	Dérivés de lactame
US4950681A (en)	1990-08-21	Ketone derivatives
US4859662A (en)	1989-08-22	Tetrahydro-imidazolylmethylcarbazolones and analogs thereof for treating 5-HT function disturbances
US5006544A (en)	1991-04-09	Imidazole derivatives and pharmaceutical use thereof
US5116984A (en)	1992-05-26	Imidazole derivatives
US5008272A (en)	1991-04-16	Lactam derivatives
US4939144A (en)	1990-07-03	Tricyclic ketone derivatives as 5-HT antagonists
EP0276163B1 (fr)	1992-07-15	Dérivés d'indole
CA2009745A1 (fr)	1990-08-10	Derives de l'indole
US5202343A (en)	1993-04-13	Tricyclic ketones useful as HT3 -receptor antagonists
JP2941702B2 (ja)	1999-08-30	５‐ｈｔ３レセプターにおいて５‐ｈｔの作用に拮抗するラクタム誘導体を含む医薬組成物
JPH0378862B2 (fr)	1991-12-17
EP0345956B1 (fr)	1994-03-16	Cétones tricycliques
WO1997017337A1 (fr)	1997-05-15	Derives substitues de 1-indolylpropyl-4-benzyl-tetrahydropyridine
NZ232598A (en)	1992-07-28	Imidazolylmethyl tetracyclic lactam derivatives and pharmaceutical compositions

Legal Events

Date	Code	Title	Description
1993-11-17	SPCF	Request for grant of supplementary protection certificate	Free format text: SPC 39/93:19930609
1996-01-24	SPCG	Supplementary protection certificate granted	Free format text: SPC 39/93 EXPIRES:20050224
2003-03-19	SPCG	Supplementary protection certificate granted	Free format text: ERROR: JOURNAL 1778 (19960124) SHOWED AN INCORRECT SPC EXPIRY DATE Spc suppl protection certif: 1993/039 Expiry date: 20050222
2005-02-23	MK9A	Patent expired