WO1998049131A1 - Neue benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel - Google Patents
Neue benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel Download PDFInfo
- Publication number
- WO1998049131A1 WO1998049131A1 PCT/EP1998/002530 EP9802530W WO9849131A1 WO 1998049131 A1 WO1998049131 A1 WO 1998049131A1 EP 9802530 W EP9802530 W EP 9802530W WO 9849131 A1 WO9849131 A1 WO 9849131A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- compounds
- phenyl
- general formula
- optionally
- Prior art date
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- XGEDYLAYYSKWPQ-UHFFFAOYSA-N CC(C)(C)Oc(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 Chemical compound CC(C)(C)Oc(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 XGEDYLAYYSKWPQ-UHFFFAOYSA-N 0.000 description 1
- JYKWUYGMZYGXNW-UHFFFAOYSA-N CC(C)(c(cc1)ccc1C(N1CCCCC1)=O)c(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 Chemical compound CC(C)(c(cc1)ccc1C(N1CCCCC1)=O)c(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 JYKWUYGMZYGXNW-UHFFFAOYSA-N 0.000 description 1
- ZZPYYXSMTTWYDL-UHFFFAOYSA-N CC(C)(c(cc1)ccc1O)c(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 Chemical compound CC(C)(c(cc1)ccc1O)c(cc1)ccc1OCc1cc(COc2ccc(CN)cc2)ccc1 ZZPYYXSMTTWYDL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07C217/56—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- 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
- C07C217/56—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Definitions
- the present invention relates to new benzylamine derivatives and phenylethylamine derivatives, processes for their preparation and their use as medicaments.
- the benzyl or phenylethylamine derivatives according to the invention correspond to the general formula I.
- R 1 is H, F, Cl, Br, J, Ci -Cß-alkyl, OH, OC ⁇ Ce-alkyl, CF 3 ;
- R5 H C-
- R a H, C-
- R 6 H C-
- R 7 H C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, - (CH 2 ) z COOR 8 , - (CH 2 ) z OR 8 , CF 3 ; z is an integer 0, 1, 2, 3 or 4, where R 6 and R 7 can optionally form a C 3 -C 6 cycloalkyl ring with one another; R 8 H, Ci-Ce alkyl;
- I, m, n is an integer 0, 1, 2, 3 or 4 where l + m + n ⁇ 4; R d -C -6-alkyl, phenyl,
- R 3 and R4 both together cannot denote hydrogen.
- R 2 H, F, Cl, Br, J, -C-C 6 alkyl, OH, O-Ci -C ⁇ -alkyl, CF 3 ;
- R 6 H Ci-04 alkyl, CF 3 ;
- B phenyl optionally substituted up to twice with F, Cl, Br, J, R a , OR c , CF 3 ;
- R c is H, Ci-C ⁇ -alkyl, COORd, CORd or a group of the formula
- I, m, n is an integer 0, 1, 2, 3 or 4 where l + m + n ⁇ 4; Rd -C -C 6 alkyl, phenyl
- C 1 -C 4 -alkyl, C 1 -C 4 -alkyl or C 1 -C 8 -alkyl generally represents a branched or unbranched hydrocarbon radical having 1 to 4 or 6 or 8 carbon atoms, optionally with one or more Halogen atom (s) - preferably fluorine - may be substituted, which may be the same or different from one another.
- lower alkyl radicals having 1 to 4 carbon atoms such as methyl; Ethyl, propyl, isopropyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl.
- the compounds of the formula I according to the invention are distinguished by a wide range of possible uses in the therapeutic field and by their oral activity. Emphasis should be placed on those applications for which the LTB4 receptor antagonistic properties play a role. The following are particularly worth mentioning:
- Chronic obstructive pulmonary diseases e.g. chronic bronchitis, psoriasis, ulcerative colitis, gastro- or enteropathy induced by non-steroidal anti-inflammatory drugs, cystic fibrosis, Alzheimer's disease, shock, reperfusion damage / ischemia, atherosclerosis, multiple sclerosis.
- the new compounds can also be used to treat diseases or conditions in which the passage of cells from the blood via the vascular endothelium into the tissue is important (for example metastasis) or diseases and conditions in which the combination of LTB4 or another molecule (for example 12-HETE) with the LTB4 receptor has an influence on cell proliferation (for example chronic myelocytic leukemia).
- the new compounds can also be used in combination with other active compounds, for example those which are used for the same indications, or for example with antiallergics, secretolytics, ⁇ -adrenergics, inhalable steroids, antihistamines and / or PAF antagonists, NSAIDs and glucocorticoids.
- Administration can be topical, oral, transdermal, nasal, parenteral or inhalative.
- Tests are suitable for pharmacological and biochemical analysis of the relationships of action, as are shown, for example, in WO 93/16036, pages 15 to 17, to which reference is made here.
- the therapeutic or prophylactic dose is - apart from the potency of the individual compounds and the body weight of the patient - dependent on the nature and seriousness of the disease.
- the dose is between 1 and 500 mg, preferably between 20 and 250 mg.
- the dose is between about 0.5 and 25, preferably between about 2 and 20 mg of active ingredient are administered to the patient.
- Inhalation solutions generally contain between about 0.5 and 5% active ingredient.
- the new compounds can be administered in customary preparations, for example as tablets, dragées, capsules, wafers, powders, granules, solutions, emulsions, syrups, inhalation aerosols, ointments, suppositories.
- composition active ingredient according to the invention 20 parts by weight of stearic acid 6 parts by weight of glucose 474 parts by weight
- the ingredients are processed in the usual way to tablets of 500 mg weight. If desired, the active substance content can be increased or decreased and the amount of glucose reduced or increased accordingly.
- composition active ingredient according to the invention 100 parts by weight of lactose, powdered 45 parts by weight of cocoa butter 1555 parts by weight
- the ingredients are processed in the usual way to form suppositories weighing 1.7 g.
- Micronized active ingredient powder (compound of formula I; particle size approx. 0.5 to 7 ⁇ m) is filled into hard gelatin capsules in an amount of 5 mg, optionally with the addition of micronized lactose.
- the powder is made usual inhalation devices, for example according to DE-A 33 45 722, to which reference is hereby made, inhaled.
- the compounds according to the invention are, inter alia, starting from compounds known from the prior art. can be prepared by the methods described in the following examples. Different, different configurations of the methods will become apparent to the person skilled in the art from the present description. However, it is expressly pointed out that these examples and the description associated with them are only intended for the purpose of illustration and are not to be regarded as a limitation of the invention.
- the compounds of the invention can be obtained from the corresponding nitrile compounds by reduction, either by catalytic hydrogenation in solvents such as methanol, ethanol, higher alcohols, DMF, water with catalysts such as Raney nickel, Pd / C, platinum, or with hydride reagents -
- solvents such as methanol, ethanol, higher alcohols, DMF, water with catalysts such as Raney nickel, Pd / C, platinum, or with hydride reagents -
- complex hydrides - such as NaBH4, Ca (BH4), LiAIH4 and other aluminum or boron hydrides at temperatures from 0 - 100 ° C and pressures of 760 Torr upwards (Example 1).
- the compounds can also be prepared from chloromethyl compounds of the formula (II) or corresponding compounds with a nucleofugic leaving group such as halogen, alkyl or aryl sulfonate, with aminoalkylphenols (III) with basic auxiliaries such as hydroxides, alcoholates, carbonates in polar solvents such as DMF, acetonitrile or ethanol (Example 2).
- a nucleofugic leaving group such as halogen, alkyl or aryl sulfonate
- aminoalkylphenols (III) with basic auxiliaries such as hydroxides, alcoholates, carbonates in polar solvents such as DMF, acetonitrile or ethanol
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (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)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP54660998A JP4049826B2 (ja) | 1997-04-30 | 1998-04-29 | 新規ベンジルアミン誘導体及びフェニルエチルアミン誘導体、それらの製造方法及び医薬組成物としての使用 |
CA002287991A CA2287991C (en) | 1997-04-30 | 1998-04-29 | New benzylamine derivatives and phenylethylamine derivatives, process for preparing them and their use as medicaments |
AT98925500T ATE259777T1 (de) | 1997-04-30 | 1998-04-29 | Benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
DE59810800T DE59810800D1 (de) | 1997-04-30 | 1998-04-29 | Benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
EP98925500A EP0980351B1 (de) | 1997-04-30 | 1998-04-29 | Benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
AU77600/98A AU7760098A (en) | 1997-04-30 | 1998-04-29 | New benzylamine and phenylethylamine derivatives, processes for preparing the same and their use as medicaments |
US09/423,160 US6288277B1 (en) | 1997-04-30 | 1998-11-05 | Benzylamine and phenylethylamine derivatives, processes for preparing the same and their use as medicaments |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19718334.4 | 1997-04-30 | ||
DE19718334A DE19718334A1 (de) | 1997-04-30 | 1997-04-30 | Neue Benzylaminderivate und Phenylethylaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998049131A1 true WO1998049131A1 (de) | 1998-11-05 |
Family
ID=7828268
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/002530 WO1998049131A1 (de) | 1997-04-30 | 1998-04-29 | Neue benzylaminderivate und phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Country Status (14)
Country | Link |
---|---|
US (1) | US6288277B1 (de) |
EP (1) | EP0980351B1 (de) |
JP (1) | JP4049826B2 (de) |
AR (1) | AR011469A1 (de) |
AT (1) | ATE259777T1 (de) |
AU (1) | AU7760098A (de) |
CA (1) | CA2287991C (de) |
CO (1) | CO4950516A1 (de) |
DE (2) | DE19718334A1 (de) |
DK (1) | DK0980351T3 (de) |
ES (1) | ES2214711T3 (de) |
PT (1) | PT980351E (de) |
WO (1) | WO1998049131A1 (de) |
ZA (1) | ZA983523B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000007977A1 (de) * | 1998-07-31 | 2000-02-17 | Boehringer Ingelheim Pharma Kg | Neue phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6528491B2 (en) * | 2000-10-24 | 2003-03-04 | Boehringer Ingelheim Pharma Kg | Pyranoside derivatives |
SI1511740T1 (sl) * | 2002-05-29 | 2009-12-31 | Lilly Co Eli | Modulatorji vitamin d receptorja tipa fenil-tiofen |
ATE370941T1 (de) * | 2003-11-20 | 2007-09-15 | Lilly Co Eli | Modulatoren des vitamin-d-rezeptors |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4424713A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
DE4424714A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Neue chemische Verbindung, ihre Herstellung und ihre Verwendung als Arnzneistoff |
-
1997
- 1997-04-30 DE DE19718334A patent/DE19718334A1/de not_active Withdrawn
-
1998
- 1998-04-28 ZA ZA983523A patent/ZA983523B/xx unknown
- 1998-04-29 PT PT98925500T patent/PT980351E/pt unknown
- 1998-04-29 ES ES98925500T patent/ES2214711T3/es not_active Expired - Lifetime
- 1998-04-29 EP EP98925500A patent/EP0980351B1/de not_active Expired - Lifetime
- 1998-04-29 CA CA002287991A patent/CA2287991C/en not_active Expired - Fee Related
- 1998-04-29 AU AU77600/98A patent/AU7760098A/en not_active Abandoned
- 1998-04-29 AT AT98925500T patent/ATE259777T1/de active
- 1998-04-29 CO CO98023627A patent/CO4950516A1/es unknown
- 1998-04-29 AR ARP980101977A patent/AR011469A1/es active Pending
- 1998-04-29 JP JP54660998A patent/JP4049826B2/ja not_active Expired - Fee Related
- 1998-04-29 DK DK98925500T patent/DK0980351T3/da active
- 1998-04-29 DE DE59810800T patent/DE59810800D1/de not_active Expired - Lifetime
- 1998-04-29 WO PCT/EP1998/002530 patent/WO1998049131A1/de active IP Right Grant
- 1998-11-05 US US09/423,160 patent/US6288277B1/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4424713A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
DE4424714A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Neue chemische Verbindung, ihre Herstellung und ihre Verwendung als Arnzneistoff |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000007977A1 (de) * | 1998-07-31 | 2000-02-17 | Boehringer Ingelheim Pharma Kg | Neue phenylethylaminderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
US6133479A (en) * | 1998-07-31 | 2000-10-17 | Boehringer Ingelheim Pharma Kg | Phenylethylamine derivatives, processes for preparing them and their use as pharmaceutical compositions |
Also Published As
Publication number | Publication date |
---|---|
DE59810800D1 (de) | 2004-03-25 |
ZA983523B (en) | 1998-10-30 |
EP0980351A1 (de) | 2000-02-23 |
DK0980351T3 (da) | 2004-05-10 |
JP4049826B2 (ja) | 2008-02-20 |
DE19718334A1 (de) | 1998-11-05 |
EP0980351B1 (de) | 2004-02-18 |
ES2214711T3 (es) | 2004-09-16 |
PT980351E (pt) | 2004-07-30 |
CO4950516A1 (es) | 2000-09-01 |
CA2287991A1 (en) | 1998-11-05 |
JP2001524966A (ja) | 2001-12-04 |
AU7760098A (en) | 1998-11-24 |
CA2287991C (en) | 2007-09-18 |
ATE259777T1 (de) | 2004-03-15 |
AR011469A1 (es) | 2000-08-16 |
US6288277B1 (en) | 2001-09-11 |
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