CA1227802A - Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation - Google Patents

Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation

Info

Publication number: CA1227802A
Authority: CA; Canada
Prior art keywords: compound; formula; atoms; acid; cis
Prior art date: 1982-03-23
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

CA000516572A

Other languages

English (en)

Inventor

Hansjorg Urbach

Rainer Henning

Volker Teetz

Hans Wissmann

Reinhard Becker

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.)

Hoechst AG

Original Assignee

Hoechst 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.)

1982-03-23

Filing date

1986-08-21

Publication date

1987-10-06

1982-03-23 Priority claimed from DE19823210496 external-priority patent/DE3210496A1/de

1986-08-21 Application filed by Hoechst AG filed Critical Hoechst AG

1986-08-21 Priority to CA000516572A priority Critical patent/CA1227802A/fr

1987-10-06 Application granted granted Critical

1987-10-06 Publication of CA1227802A publication Critical patent/CA1227802A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 49
238000002360 preparation method Methods 0.000 title claims abstract description 12
-1 of bicyclic aminoacids Chemical class 0.000 title description 20
235000001014 amino acid Nutrition 0.000 title 1
239000000543 intermediate Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 119
239000002253 acid Substances 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 37
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 4
238000000926 separation method Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 1
125000004104 aryloxy group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
239000000243 solution Substances 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
150000003254 radicals Chemical class 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
150000003839 salts Chemical class 0.000 description 14
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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239000002585 base Substances 0.000 description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
244000298715 Actinidia chinensis Species 0.000 description 6
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235000009436 Actinidia deliciosa Nutrition 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
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238000001704 evaporation Methods 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
241000282320 Panthera leo Species 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 5
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
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229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
229960003767 alanine Drugs 0.000 description 4
229920000180 alkyd Polymers 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 3
JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
125000000041 C6-C10 aryl group Chemical group 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
235000018936 Vitellaria paradoxa Nutrition 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
WNNNWFKQCKFSDK-BYPYZUCNSA-N (2s)-2-aminopent-4-enoic acid Chemical compound OC(=O)[C@@H](N)CC=C WNNNWFKQCKFSDK-BYPYZUCNSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003862 amino acid derivatives Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
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230000000694 effects Effects 0.000 description 2
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229910052736 halogen Inorganic materials 0.000 description 2
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150000002500 ions Chemical class 0.000 description 2
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
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JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
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STPXIOGYOLJXMZ-UHFFFAOYSA-N ethyl 2-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=CC=C1 STPXIOGYOLJXMZ-UHFFFAOYSA-N 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
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125000002950 monocyclic group Chemical group 0.000 description 1
QEWYKACRFQMRMB-UHFFFAOYSA-N monofluoroacetic acid Natural products OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 1
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150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
150000002989 phenols Chemical class 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
239000010773 plant oil Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
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235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
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239000011593 sulfur Substances 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000563 toxic property Toxicity 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
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000013022 venting Methods 0.000 description 1

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Indole Compounds (AREA)

CA000516572A 1982-03-23 1986-08-21 Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation Expired CA1227802A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000516572A CA1227802A (fr)	1982-03-23	1986-08-21	Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19823210496 DE3210496A1 (de)	1982-03-23	1982-03-23	Neue derivate bicyclischer aminsaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie neue bicyclische aminosaeuren als zwischenstufen und verfahren zu deren herstellung
DEP3210496.0		1982-03-23
CA000424127A CA1223868A (fr)	1982-03-23	1983-03-22	Derives d'amino-acides bicycliques; preparation; agents renfermant ces derives et leur utilisation; nouveaux amino-acides bicycliques, produits intermediaires, et leur preparation
CA000516572A CA1227802A (fr)	1982-03-23	1986-08-21	Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000424127A Division CA1223868A (fr)	1982-03-23	1983-03-22	Derives d'amino-acides bicycliques; preparation; agents renfermant ces derives et leur utilisation; nouveaux amino-acides bicycliques, produits intermediaires, et leur preparation

Publications (1)

Publication Number	Publication Date
CA1227802A true CA1227802A (fr)	1987-10-06

Family

ID=25669976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000516572A Expired CA1227802A (fr)	1982-03-23	1986-08-21	Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation

Country Status (1)

Country	Link
CA (1)	CA1227802A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117643897A (zh) *	2024-01-29	2024-03-05	成都岷山绿氢能源有限公司	用于n-杂环的选择性半氢化催化剂及其制备方法

1986
- 1986-08-21 CA CA000516572A patent/CA1227802A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117643897A (zh) *	2024-01-29	2024-03-05	成都岷山绿氢能源有限公司	用于n-杂环的选择性半氢化催化剂及其制备方法
CN117643897B (zh) *	2024-01-29	2024-05-03	成都岷山绿氢能源有限公司	用于n-杂环的选择性半氢化催化剂及其制备方法

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Date	Code	Title	Description
2004-10-06	MKEX	Expiry

Publication	Publication Date	Title
US4668797A (en)	1987-05-26	Bicyclic aminoacids as intermediates and processes for their preparation
EP0354583B1 (fr)	1993-11-03	Dérivés du DC-88A
AU2016217496B2 (en)	2019-03-07	Crystalline forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide
NZ201779A (en)	1986-01-24	N-ethanoic acid-n'-alkanoic acid-urea derivatives
CZ576590A3 (en)	1995-11-15	Derivatives of amino acids, process of their preparation, their use and medicaments based thereon
JPH01301659A (ja)	1989-12-05	新規な二環式化合物
CZ471190A3 (cs)	2000-08-16	Inhibitory retrovirálních proteáz
CA2121391A1 (fr)	1994-10-29	Derives d'indoloylguanidine
EP0319429B1 (fr)	1994-04-27	Dérivés de la 9-(acylamino)tétrahydroacridine et agents pour l'amélioration de la mémoire les contenant comme ingrédient
NZ206574A (en)	1987-03-06	1-(n-(1-carboxyalkyl)-alpha-aminoalkanoyl)-octahydro2s,3as,8as-cyclohepta(b)pyrrol-2-ylcarboxylic acid derivatives
NZ236550A (en)	1992-05-26	Indole-substituted polyamines and pharmaceutical compositions
EP0070562B1 (fr)	1985-06-12	Dérivés d'ergoline, leur procédé de préparation et compositions pharmaceutiques les contenant
EP0480061B1 (fr)	1996-12-04	Inhibiteur de troubles hepatiques
LV11619B (en)	1997-04-20	Novel crystal form of anhydrous 7-(£1a,5a,6a\|-6-amino-3-azabicyclo£3.1.0\|hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonic acid salt
EP0068173B1 (fr)	1984-09-26	Dérivés de perhydro-1,4-thiazépine-5-one et de perhydro-1,4-thiazocine-5-one, leur procédé de préparation et compositions pharmaceutiques les contenant
HU203891B (en)	1991-10-28	Process for producing pyrrolidino-piperazine-dion derivatives and pharmaceutical compositions contianing them as active components
US5635511A (en)	1997-06-03	Treatment of heart rhythm disorders by administration of 3-phenylsulfonyl-3,7-diazabicyclo[3.3.1]nonane compounds.
CA1227802A (fr)	1987-10-06	Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation
US4143134A (en)	1979-03-06	Halo-phosphonopeptides
HU198052B (en)	1989-07-28	Process for producing purine derivatives substituted by side chain containing piperazinyl ring and pharmaceutical compositions comprising such compounds
EP0057998B1 (fr)	1984-08-08	Composés alicycliques, leur préparation et utilisation
US4250180A (en)	1981-02-10	Method of treating arrhythmia
JPH08259532A (ja)	1996-10-08	ペプチド様化合物又はその薬理的に許容される塩
JPS6045577A (ja)	1985-03-12	２−アザビシクロ〔２．２．２〕オクタン誘導体
IE66009B1 (en)	1995-11-29	New substituted amino acid derivatives process for preparing these and pharmaceutical compositions containing them