DD218359A5 - Verfahren zur herstellung von 3-(5-aminopenthyl)-amino-1-benzazepin-2-on-1-alkansaeuren - Google Patents

Verfahren zur herstellung von 3-(5-aminopenthyl)-amino-1-benzazepin-2-on-1-alkansaeuren Download PDF

Info

Publication number: DD218359A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; cor; hydroxy; groups
Prior art date: 1983-02-10

Application number

DD84259979A

Other languages

German (de)

English (en)

Inventor

Jeffry W H Watthey

Stephen K Boyer

Joseph Bach

Gottfried Sedelmeier

Original Assignee

Ciba Geigy 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.)

1983-02-10

Filing date

1984-02-09

Publication date

1985-02-06

1984-02-09 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1985-02-06 Publication of DD218359A5 publication Critical patent/DD218359A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 169
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 67
150000003839 salts Chemical class 0.000 claims abstract description 41
125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
-1 monocyclic lactam Chemical class 0.000 claims description 94
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 84
238000000034 method Methods 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 45
230000008569 process Effects 0.000 claims description 34
230000002829 reductive effect Effects 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 16
239000003638 chemical reducing agent Substances 0.000 claims description 15
238000009833 condensation Methods 0.000 claims description 14
230000005494 condensation Effects 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
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230000002152 alkylating effect Effects 0.000 claims 1
230000009467 reduction Effects 0.000 abstract description 26
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 abstract description 4
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000005588 protonation Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000007279 water homeostasis Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

DD84259979A 1983-02-10 1984-02-09 Verfahren zur herstellung von 3-(5-aminopenthyl)-amino-1-benzazepin-2-on-1-alkansaeuren DD218359A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/465,695 US4473575A (en)	1982-07-19	1983-02-10	3-Amino-(1)-benzazepin-2-one-1-alkanoic acids

Publications (1)

Publication Number	Publication Date
DD218359A5 true DD218359A5 (de)	1985-02-06

Family

ID=23848805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84259979A DD218359A5 (de)	1983-02-10	1984-02-09	Verfahren zur herstellung von 3-(5-aminopenthyl)-amino-1-benzazepin-2-on-1-alkansaeuren

Country Status (24)

Country	Link
US (1)	US4473575A (fr)
EP (2)	EP0119955B1 (fr)
JP (2)	JPS59172473A (fr)
KR (1)	KR900009023B1 (fr)
AR (8)	AR242564A1 (fr)
AT (2)	ATE48598T1 (fr)
AU (1)	AU574061B2 (fr)
CA (2)	CA1225397A (fr)
CY (1)	CY1674A (fr)
DD (1)	DD218359A5 (fr)
DE (2)	DE3481612D1 (fr)
DK (2)	DK171257B1 (fr)
ES (10)	ES8707216A1 (fr)
FI (1)	FI77857C (fr)
GR (1)	GR79809B (fr)
HK (1)	HK97592A (fr)
HU (1)	HU192394B (fr)
IE (1)	IE56858B1 (fr)
IL (1)	IL70881A (fr)
NO (1)	NO166232C (fr)
NZ (1)	NZ207091A (fr)
PT (1)	PT78075B (fr)
SG (1)	SG94992G (fr)
ZA (1)	ZA84958B (fr)

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ZA825779B (en) *	1981-08-11	1984-04-25	Ciba Geigy Ag	Benzazepins-2-ones
US4410520A (en) *	1981-11-09	1983-10-18	Ciba-Geigy Corporation	3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
US4473575A (en) *	1982-07-19	1984-09-25	Ciba-Geigy Corporation	3-Amino-(1)-benzazepin-2-one-1-alkanoic acids
EP0107095B1 (fr) *	1982-09-30	1987-09-09	Merck & Co. Inc.	1-N-carboxyalkyl-benzolactames utiles comme agents antihypertensifs

1983
- 1983-02-10 US US06/465,695 patent/US4473575A/en not_active Expired - Lifetime
1984
- 1984-02-06 AT AT84810072T patent/ATE48598T1/de active
- 1984-02-06 AT AT84810071T patent/ATE50989T1/de active
- 1984-02-06 DE DE8484810071T patent/DE3481612D1/de not_active Expired - Lifetime
- 1984-02-06 EP EP84810072A patent/EP0119955B1/fr not_active Expired
- 1984-02-06 DE DE8484810072T patent/DE3480705D1/de not_active Expired - Lifetime
- 1984-02-06 EP EP84810071A patent/EP0119954B1/fr not_active Expired - Lifetime
- 1984-02-07 IL IL70881A patent/IL70881A/xx not_active IP Right Cessation
- 1984-02-08 GR GR73754A patent/GR79809B/el unknown
- 1984-02-08 CA CA000446971A patent/CA1225397A/fr not_active Expired
- 1984-02-08 FI FI840513A patent/FI77857C/fi not_active IP Right Cessation
- 1984-02-08 PT PT78075A patent/PT78075B/pt not_active IP Right Cessation
- 1984-02-08 CA CA000446970A patent/CA1218993A/fr not_active Expired
- 1984-02-09 DK DK058284A patent/DK171257B1/da not_active IP Right Cessation
- 1984-02-09 DK DK58184A patent/DK58184A/da not_active Application Discontinuation
- 1984-02-09 NO NO840487A patent/NO166232C/no unknown
- 1984-02-09 ZA ZA84958A patent/ZA84958B/xx unknown
- 1984-02-09 DD DD84259979A patent/DD218359A5/de not_active IP Right Cessation
- 1984-02-09 ES ES529595A patent/ES8707216A1/es not_active Expired
- 1984-02-09 NZ NZ207091A patent/NZ207091A/en unknown
- 1984-02-09 ES ES529594A patent/ES8609261A1/es not_active Expired
- 1984-02-09 JP JP59020905A patent/JPS59172473A/ja active Granted
- 1984-02-09 HU HU84523A patent/HU192394B/hu not_active IP Right Cessation
- 1984-02-09 AU AU24430/84A patent/AU574061B2/en not_active Ceased
- 1984-02-09 IE IE302/84A patent/IE56858B1/en not_active IP Right Cessation
- 1984-02-10 AR AR84295689A patent/AR242564A1/es active
- 1984-02-10 KR KR1019840000630A patent/KR900009023B1/ko not_active Expired
- 1984-02-10 JP JP59022031A patent/JPS59172475A/ja active Granted
1985
- 1985-06-13 ES ES544127A patent/ES8702363A1/es not_active Expired
- 1985-06-17 ES ES544257A patent/ES8609263A1/es not_active Expired
- 1985-06-17 ES ES544254A patent/ES8703859A1/es not_active Expired
- 1985-06-17 ES ES544255A patent/ES8609262A1/es not_active Expired
- 1985-06-17 ES ES544258A patent/ES8609264A1/es not_active Expired
- 1985-06-17 ES ES544259A patent/ES8700239A1/es not_active Expired
- 1985-06-17 ES ES544256A patent/ES8705409A1/es not_active Expired
- 1985-06-17 ES ES544260A patent/ES8609265A1/es not_active Expired
1986
- 1986-08-15 AR AR86304922A patent/AR243165A1/es active
- 1986-08-15 AR AR86304926A patent/AR243161A1/es active
- 1986-08-15 AR AR86304925A patent/AR243162A1/es active
- 1986-08-15 AR AR86304921A patent/AR242191A1/es active
- 1986-08-15 AR AR86304920A patent/AR242190A1/es active
- 1986-08-15 AR AR86304924A patent/AR243163A1/es active
- 1986-08-15 AR AR86304923A patent/AR243164A1/es active
1992
- 1992-09-21 SG SG949/92A patent/SG94992G/en unknown
- 1992-12-03 HK HK975/92A patent/HK97592A/xx not_active IP Right Cessation
1993
- 1993-10-10 CY CY1674A patent/CY1674A/xx unknown

Also Published As

Publication number	Publication date
ES8700239A1 (es)	1986-10-16
DE3481612D1 (de)	1990-04-19
DK58184A (da)	1984-08-11
ES529595A0 (es)	1987-07-16
AR243165A1 (es)	1993-07-30
HK97592A (en)	1992-12-11
ES8702363A1 (es)	1987-01-01
AR243162A1 (es)	1993-07-30
DE3480705D1 (de)	1990-01-18
DK58284A (da)	1984-08-11
JPH0460108B2 (fr)	1992-09-25
FI840513A0 (fi)	1984-02-08
ES544259A0 (es)	1986-10-16
ES544258A0 (es)	1986-09-01
GR79809B (fr)	1984-10-31
ES544260A0 (es)	1986-09-01
ATE48598T1 (de)	1989-12-15
EP0119954A3 (en)	1986-06-11
US4473575A (en)	1984-09-25
ES8609264A1 (es)	1986-09-01
DK58184D0 (da)	1984-02-09
ES529594A0 (es)	1986-07-16
AR242190A1 (es)	1993-03-31
JPS59172473A (ja)	1984-09-29
ES544254A0 (es)	1987-03-01
ES544127A0 (es)	1987-01-01
ES544256A0 (es)	1987-05-01
IL70881A (en)	1987-10-30
ES8703859A1 (es)	1987-03-01
FI77857B (fi)	1989-01-31
AR243164A1 (es)	1993-07-30
ES8707216A1 (es)	1987-07-16
IL70881A0 (en)	1984-05-31
AU574061B2 (en)	1988-06-30
KR840007722A (ko)	1984-12-10
CA1225397A (fr)	1987-08-11
AR242191A1 (es)	1993-03-31
ES8705409A1 (es)	1987-05-01
ZA84958B (en)	1984-09-26
PT78075B (en)	1986-06-11
SG94992G (en)	1992-12-04
JPS59172475A (ja)	1984-09-29
AR242564A1 (es)	1993-04-30
ATE50989T1 (de)	1990-03-15
IE840302L (en)	1984-08-10
EP0119955A2 (fr)	1984-09-26
DK171257B1 (da)	1996-08-12
AR243163A1 (es)	1993-07-30
PT78075A (en)	1984-03-01
NO166232B (no)	1991-03-11
ES8609263A1 (es)	1986-09-01
CA1218993A (fr)	1987-03-10
IE56858B1 (en)	1992-01-01
FI840513L (fi)	1984-08-11
EP0119954A2 (fr)	1984-09-26
ES8609262A1 (es)	1986-09-01
ES8609261A1 (es)	1986-07-16
EP0119954B1 (fr)	1990-03-14
EP0119955A3 (en)	1986-06-11
ES544255A0 (es)	1986-09-01
JPH0421665B2 (fr)	1992-04-13
NZ207091A (en)	1985-11-08
NO166232C (no)	1991-06-19
EP0119955B1 (fr)	1989-12-13
CY1674A (en)	1993-10-10
DK58284D0 (da)	1984-02-09
ES544257A0 (es)	1986-09-01
ES8609265A1 (es)	1986-09-01
AR243161A1 (es)	1993-07-30
KR900009023B1 (ko)	1990-12-17
AU2443084A (en)	1984-08-16
NO840487L (no)	1984-08-13
HU192394B (en)	1987-06-29
FI77857C (fi)	1989-05-10

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0119955B1 (fr)	1989-12-13	Acides 3-(5-aminopentyl)-amino-1-benzazépine-2-one-1-alkanoiques, leur procédé de préparation, les préparations pharmaceutiques les contenant de même que leur emploi thérapeutique
EP0072352B1 (fr)	1986-03-05	Benzazepin-2-ones, procédé pour leur préparation, préparations pharmaceutiques contenant ces composés ainsi que ces composés pour utilisation thérapeutique
EP0119161B1 (fr)	1989-06-28	Dérivés de benzazocinone et benzazoninon, leur procédé de préparation, préparations pharmaceutiques contenant ces composés, et leur application thérapeutique
EP0111873B1 (fr)	1987-10-07	Dérivés de l'acide cis, endo-aza-2 bicyclo(5.3.0)décane-carboxylique-3, procédé pour leur préparation, compositions les contenant et leur application
EP0150263B1 (fr)	1990-06-20	Dérivés de l'acide cis, endo-2-azabicyclo-[3.3.0]-octane-3-carboxylique, procédé pour leur préparation, médicaments les contenant et leur application
EP0184550B1 (fr)	1992-03-18	Dérivés de 5-amino-4-hydroxy valérylamides
EP0089637B1 (fr)	1986-10-15	Dérivés d'amino acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation, ainsi que des amino acides bicycliques comme produits intermédiaires et procédé pour leur préparation
EP0871653A1 (fr)	1998-10-21	Nouveaux derives d'acide amine, procede de production correspondant et compositions pharmaceutiques contenant ces composes
DD236522A5 (de)	1986-06-11	Verfahren zur herstellung medizinisch wertvoller verbindungen und zwischenverbindungen
IE50298B1 (en)	1986-03-19	Long lasting agonists and antagonists of lhrh and compositions containing them
DE3885252T2 (de)	1994-02-17	Nichtpeptidische Renin-Hemmer.
EP0374098A2 (fr)	1990-06-20	Inhibiteurs de protéase rétrovirale
DE3209708A1 (de)	1982-10-21	Peptidderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE3606448A1 (de)	1986-08-28	Aminoalkanoylureidoamino- und -iminosaeure-verbindungen
DE69015437T2 (de)	1995-05-04	Amino-substituierte Heterocyclen als Renininhibitoren.
DE2718718A1 (de)	1977-11-17	Somatostatinanaloge und zwischenprodukte hierzu
DE3325850A1 (de)	1984-01-19	Substituierte peptide
DE3850818T2 (de)	1994-11-17	Fluor enthaltende Renin-Inhibitoren.
EP0203450B1 (fr)	1992-04-01	Dérivés d'amino-acides bicycliques, leur procédé de préparation, les agents les contenant et leur emploi
DE3423743A1 (de)	1985-01-10	Benzothiazepin-derivate und verfahren zu ihrer herstellung
DE2063996A1 (de)	1971-07-15	Neue Tuberkulostatisch wirkende alpha Aminoxy hydroxamsaurederivate und Verfahren zur Herstellung derselben
DE3426720A1 (de)	1986-01-23	Benzthiazepinon- und benzthiazocinon-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung, sowie zwischenprodukte bei ihrer herstellung
DE3708484A1 (de)	1987-09-24	Neue 3-(3-cycloalkylpropyl)amino-1-benzazepin-2-on-1-alkansaeuren
DE69706206T2 (de)	2002-05-23	Von Neurokininen abgeleitete Pseudopeptide, Verfahren für ihre Herstellung und sie enthaltende pharmazeutische Zubereitungen
EP0170775B2 (fr)	1994-10-12	Dérivés d'amino-acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation ainsi que d'amino-acides bicycliques comme intermédiaires et procédé pour leur préparation