MXPA04012136A - Nuevos derivados de tetrahidropiridina como inhibidores de renina. - Google Patents
Nuevos derivados de tetrahidropiridina como inhibidores de renina.Info
- Publication number
- MXPA04012136A MXPA04012136A MXPA04012136A MXPA04012136A MXPA04012136A MX PA04012136 A MXPA04012136 A MX PA04012136A MX PA04012136 A MXPA04012136 A MX PA04012136A MX PA04012136 A MXPA04012136 A MX PA04012136A MX PA04012136 A MXPA04012136 A MX PA04012136A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- tetrahydro
- carboxylic acid
- pyridine
- acid
- Prior art date
Links
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000002461 renin inhibitor Substances 0.000 title description 11
- 229940086526 renin-inhibitors Drugs 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 351
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 { 4- [3- (2-methoxybenzyloxy) propoxy] phenyl} -1, 2,5,6-tetrahydro-pyridine-3-carboxylic acid [2- (2-chlorophenyl) ethyl] methylamide Chemical compound 0.000 claims description 550
- 239000002253 acid Substances 0.000 claims description 316
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 166
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 114
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 103
- QMDFHZOGAYONLN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-3-carboxylic acid Chemical compound OC(=O)C1CNC=CC1 QMDFHZOGAYONLN-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 57
- GCJYLAWVUWEHLW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC=C1CNC1CC1 GCJYLAWVUWEHLW-UHFFFAOYSA-N 0.000 claims description 46
- 239000011664 nicotinic acid Substances 0.000 claims description 43
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 39
- 239000002904 solvent Chemical class 0.000 claims description 37
- CRIMYHBFDHWKQY-UHFFFAOYSA-N n-[(2,3-dimethylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC(CNC2CC2)=C1C CRIMYHBFDHWKQY-UHFFFAOYSA-N 0.000 claims description 36
- KJYVKUQRRKDPAX-UHFFFAOYSA-N n-[(2,3-dichlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1Cl KJYVKUQRRKDPAX-UHFFFAOYSA-N 0.000 claims description 34
- CEQDKNLDFWAMEL-UHFFFAOYSA-N n-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)C1=CC=CC(CNC2CC2)=C1Cl CEQDKNLDFWAMEL-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 25
- BTBDLUOYLCXSMK-UHFFFAOYSA-N n-[(3,5-dimethoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC(OC)=CC(CNC2CC2)=C1 BTBDLUOYLCXSMK-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- CUPDQCKBQJVOMC-UHFFFAOYSA-N n-[(2-fluoro-5-methoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC=C(F)C(CNC2CC2)=C1 CUPDQCKBQJVOMC-UHFFFAOYSA-N 0.000 claims description 19
- NUPAMNLYORQZRV-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC=CC(CNC2CC2)=C1 NUPAMNLYORQZRV-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 16
- 201000006370 kidney failure Diseases 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 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 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- QTDZOWFRBNTPQR-UHFFFAOYSA-N guvacine Chemical compound OC(=O)C1=CCCNC1 QTDZOWFRBNTPQR-UHFFFAOYSA-N 0.000 claims description 12
- SBKDFWWYKALTKE-UHFFFAOYSA-N n-[(2-bromophenyl)methyl]cyclopropanamine Chemical compound BrC1=CC=CC=C1CNC1CC1 SBKDFWWYKALTKE-UHFFFAOYSA-N 0.000 claims description 12
- SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 claims description 12
- 206010019280 Heart failures Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- VALINFAZSMPKJJ-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1 VALINFAZSMPKJJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- WYQUCNZBUBLJHN-UHFFFAOYSA-N n-[(2-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC=C1CNC1CC1 WYQUCNZBUBLJHN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000012876 carrier material Substances 0.000 claims description 8
- QWMNTOVGKJAROU-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=CC=C1Cl QWMNTOVGKJAROU-UHFFFAOYSA-N 0.000 claims description 8
- LJBFNXZKZYKGFY-UHFFFAOYSA-N n-[(3-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC(CNC2CC2)=C1 LJBFNXZKZYKGFY-UHFFFAOYSA-N 0.000 claims description 8
- POYWLSASJPZKQR-UHFFFAOYSA-N n-[2-(2-methylphenyl)ethyl]cyclopropanamine Chemical compound CC1=CC=CC=C1CCNC1CC1 POYWLSASJPZKQR-UHFFFAOYSA-N 0.000 claims description 8
- GEDRFLMRWRNXGV-UHFFFAOYSA-N n-[2-(4-methoxyphenoxy)ethyl]cyclopropanamine Chemical compound C1=CC(OC)=CC=C1OCCNC1CC1 GEDRFLMRWRNXGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 239000005541 ACE inhibitor Substances 0.000 claims description 7
- 206010063897 Renal ischaemia Diseases 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- ORZRHMRDNOCKDU-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]cyclopropanamine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1CC1 ORZRHMRDNOCKDU-UHFFFAOYSA-N 0.000 claims description 7
- VRDMJNOXKZMLTF-UHFFFAOYSA-N n-[(6-chloro-1,3-benzodioxol-5-yl)methyl]cyclopropanamine Chemical compound ClC1=CC=2OCOC=2C=C1CNC1CC1 VRDMJNOXKZMLTF-UHFFFAOYSA-N 0.000 claims description 7
- BNLAPXNSMIAMIO-UHFFFAOYSA-N n-[2-(4-methylphenyl)ethyl]cyclopropanamine Chemical compound C1=CC(C)=CC=C1CCNC1CC1 BNLAPXNSMIAMIO-UHFFFAOYSA-N 0.000 claims description 7
- DTJKAALGEAHUIV-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-methylethanamine Chemical compound CNCCC1=CC=CC=C1Cl DTJKAALGEAHUIV-UHFFFAOYSA-N 0.000 claims description 6
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000000877 morphologic effect Effects 0.000 claims description 6
- WRRVCXHKEDNRNB-UHFFFAOYSA-N n-[(3,5-difluorophenyl)methyl]cyclopropanamine Chemical compound FC1=CC(F)=CC(CNC2CC2)=C1 WRRVCXHKEDNRNB-UHFFFAOYSA-N 0.000 claims description 6
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 6
- DIWGZVQKFSFNLH-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1Cl DIWGZVQKFSFNLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000031225 myocardial ischemia Diseases 0.000 claims description 5
- ILHIZUJWNGLALK-UHFFFAOYSA-N n-(2-phenylethyl)cyclopropanamine Chemical compound C1CC1NCCC1=CC=CC=C1 ILHIZUJWNGLALK-UHFFFAOYSA-N 0.000 claims description 5
- WJFXKLXJOHUXCU-UHFFFAOYSA-N n-[2-(3-methoxyphenoxy)ethyl]cyclopropanamine Chemical compound COC1=CC=CC(OCCNC2CC2)=C1 WJFXKLXJOHUXCU-UHFFFAOYSA-N 0.000 claims description 5
- ANCFTHKEGKDXKD-UHFFFAOYSA-N n-[[3-(trifluoromethoxy)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)OC1=CC=CC(CNC2CC2)=C1 ANCFTHKEGKDXKD-UHFFFAOYSA-N 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000002249 Diabetes Complications Diseases 0.000 claims description 4
- 206010012655 Diabetic complications Diseases 0.000 claims description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010038419 Renal colic Diseases 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- RVXJABFVIDLTSI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]cyclopropanamine Chemical compound C1=CC(Cl)=CC=C1CNC1CC1 RVXJABFVIDLTSI-UHFFFAOYSA-N 0.000 claims description 4
- NJDGRXSBVMPMQX-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]cyclopropanamine Chemical compound C1=CC(F)=CC=C1CCNC1CC1 NJDGRXSBVMPMQX-UHFFFAOYSA-N 0.000 claims description 4
- AOMAZSZEDRDSIF-UHFFFAOYSA-N n-[[3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)C1=CC=CC(CNC2CC2)=C1 AOMAZSZEDRDSIF-UHFFFAOYSA-N 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
- NTIIWMOYVFPRJN-UHFFFAOYSA-N n-[(3-fluoro-2-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=C(F)C=CC=C1CNC1CC1 NTIIWMOYVFPRJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 2
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- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
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- INJAMPFEUYMVHZ-UHFFFAOYSA-N n-[(2,3-difluorophenyl)methyl]cyclopropanamine Chemical compound FC1=CC=CC(CNC2CC2)=C1F INJAMPFEUYMVHZ-UHFFFAOYSA-N 0.000 claims description 2
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- LUVQDOPJNGGUDF-UHFFFAOYSA-N n-[2-(3-methylphenoxy)ethyl]cyclopropanamine Chemical compound CC1=CC=CC(OCCNC2CC2)=C1 LUVQDOPJNGGUDF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
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- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
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- 239000011591 potassium Substances 0.000 claims 1
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- 238000000034 method Methods 0.000 abstract description 194
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 196
- 229910052731 fluorine Inorganic materials 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 238000000746 purification Methods 0.000 description 57
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 48
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP0207102 | 2002-06-27 | ||
| PCT/EP2003/004445 WO2004002957A1 (en) | 2002-06-27 | 2003-04-29 | Novel tetrahydropyridine derivatives as renin inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04012136A true MXPA04012136A (es) | 2005-04-19 |
Family
ID=29797098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04012136A MXPA04012136A (es) | 2002-06-27 | 2003-04-29 | Nuevos derivados de tetrahidropiridina como inhibidores de renina. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20060009497A1 (enExample) |
| EP (1) | EP1519920A1 (enExample) |
| JP (1) | JP2005532371A (enExample) |
| CN (1) | CN1662498A (enExample) |
| AU (1) | AU2003229746A1 (enExample) |
| BR (1) | BR0312000A (enExample) |
| CA (1) | CA2490138A1 (enExample) |
| CL (1) | CL2003002043A1 (enExample) |
| IL (1) | IL165887A0 (enExample) |
| MX (1) | MXPA04012136A (enExample) |
| NO (1) | NO20050290L (enExample) |
| PL (1) | PL375214A1 (enExample) |
| RU (1) | RU2005102002A (enExample) |
| TW (1) | TW200514772A (enExample) |
| WO (1) | WO2004002957A1 (enExample) |
| ZA (1) | ZA200408423B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060217371A1 (en) * | 2003-04-28 | 2006-09-28 | Olivier Bezencon | Diazabicyclononene and tetrahydropyriddine derivatives as renin inhibitors |
| MXPA05011478A (es) * | 2003-04-29 | 2005-12-12 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,6-tetrahidropiridina 3,4-disustituidos novedosos. |
| CA2521938A1 (en) * | 2003-04-30 | 2004-11-11 | Actelion Pharmaceuticals Ltd | 9-azabicyclo[3.3.1]non-6-ene derivatives with a heteroatom at the 3-position as renin inhibitors |
| EP1622564A2 (en) * | 2003-05-02 | 2006-02-08 | Actelion Pharmaceuticals Ltd. | Diazabicyclononene derivatives |
| WO2004105738A2 (en) * | 2003-05-30 | 2004-12-09 | Actelion Pharmaceuticals Ltd | Use of tetrahydropyridine derivatives |
| CN1863773A (zh) * | 2003-10-09 | 2006-11-15 | 埃科特莱茵药品有限公司 | 四氢吡啶衍生物 |
| JP2007508262A (ja) * | 2003-10-13 | 2007-04-05 | アクテリオン ファマシューティカルズ リミテッド | 新規ジアザビシクロノネン誘導体およびその使用 |
| US20070111989A1 (en) * | 2003-12-05 | 2007-05-17 | Olivier Bezencon | Novel diazabicyclononene derivatives and use |
| WO2005068427A1 (ja) * | 2004-01-14 | 2005-07-28 | Takeda Pharmaceutical Company Limited | カルボキサミド誘導体およびその用途 |
| RU2426532C2 (ru) * | 2004-03-17 | 2011-08-20 | Новартис Аг | Применение органических соединений |
| CA2577084A1 (en) | 2004-08-25 | 2006-03-02 | Olivier Bezencon | Bicyclononene derivatives as renin inhibitors |
| GB0428526D0 (en) * | 2004-12-30 | 2005-02-09 | Novartis Ag | Organic compounds |
| GB0500784D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0504850D0 (en) * | 2005-03-09 | 2005-04-13 | Novartis Ag | Organic compounds |
| GB0510810D0 (en) * | 2005-05-26 | 2005-06-29 | Novartis Ag | Organic compounds |
| AU2006253805A1 (en) * | 2005-05-27 | 2006-12-07 | Actelion Pharmaceuticals Ltd. | Novel piperidine carboxylic acid amide derivatives |
| GB0514203D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| WO2007049224A1 (en) * | 2005-10-25 | 2007-05-03 | Actelion Pharmaceuticals Ltd | Novel hexahydro- or octahydro-cyclopenta[c]pyrrole derivatives |
| RU2425032C2 (ru) | 2006-02-02 | 2011-07-27 | Актелион Фармасьютикалз Лтд | Вторичные амины в качестве ингибиторов ренина |
| CA2642424A1 (en) * | 2006-03-03 | 2007-09-07 | Actelion Pharmaceuticals Ltd. | Primary amines as renin inhibitors |
| NZ571595A (en) * | 2006-03-08 | 2010-06-25 | Actelion Pharmaceuticals Ltd | New amines |
| EP1908471A1 (en) * | 2006-10-04 | 2008-04-09 | Speedel Experimenta AG | Tetrahydropyridines as renin inhibitors |
| AU2008253519A1 (en) | 2007-05-24 | 2008-11-27 | Merck Frosst Canada Ltd | Novel case of renin inhibitors |
| EP2190811B1 (en) | 2007-08-20 | 2013-08-07 | Merck Canada Inc. | Renin inhibitors |
| US8889714B2 (en) | 2008-05-05 | 2014-11-18 | Actelion Pharmaceuticals Ltd. | 3,4-substituted piperidine derivatives as renin inhibitors |
| TWI471289B (zh) | 2010-06-11 | 2015-02-01 | Rhodes Technologies | 使三級胺進行ｎ－脫烷反應之方法 |
| CA2936749C (en) | 2010-06-11 | 2019-07-09 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
| CN117865941B (zh) * | 2024-03-13 | 2024-06-28 | 上海方予健康医药科技有限公司 | 取代哌啶化合物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376666A (en) * | 1992-11-30 | 1994-12-27 | The Du Pont Merck Pharmaceutical Company | Angiotension-II receptor blocking, azacycloalkyl or azacycloalkenyl |
| PL193686B1 (pl) * | 1995-09-07 | 2007-03-30 | Hoffmann La Roche | Pochodne piperydyny, środki lecznicze zawierającepochodne piperydyny, sposoby wytwarzania tych pochodnych oraz zastosowanie pochodnych |
| US6376672B1 (en) * | 1999-04-27 | 2002-04-23 | Hoffmann-La Roche Inc. | Naphthalenylmethoxypiperidines as renin inhibitors |
-
2003
- 2003-04-29 MX MXPA04012136A patent/MXPA04012136A/es unknown
- 2003-04-29 AU AU2003229746A patent/AU2003229746A1/en not_active Abandoned
- 2003-04-29 US US10/514,164 patent/US20060009497A1/en not_active Abandoned
- 2003-04-29 RU RU2005102002/04A patent/RU2005102002A/ru not_active Application Discontinuation
- 2003-04-29 WO PCT/EP2003/004445 patent/WO2004002957A1/en not_active Ceased
- 2003-04-29 BR BR0312000-7A patent/BR0312000A/pt not_active IP Right Cessation
- 2003-04-29 CA CA002490138A patent/CA2490138A1/en not_active Abandoned
- 2003-04-29 EP EP03722566A patent/EP1519920A1/en not_active Withdrawn
- 2003-04-29 CN CN038138875A patent/CN1662498A/zh active Pending
- 2003-04-29 PL PL03375214A patent/PL375214A1/xx not_active Application Discontinuation
- 2003-04-29 JP JP2004516551A patent/JP2005532371A/ja active Pending
- 2003-10-10 CL CL200302043A patent/CL2003002043A1/es unknown
- 2003-10-28 TW TW092129927A patent/TW200514772A/zh unknown
-
2004
- 2004-10-18 ZA ZA200408423A patent/ZA200408423B/xx unknown
- 2004-12-21 IL IL16588704A patent/IL165887A0/xx unknown
-
2005
- 2005-01-19 NO NO20050290A patent/NO20050290L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0312000A (pt) | 2005-03-22 |
| PL375214A1 (en) | 2005-11-28 |
| NO20050290L (no) | 2005-01-19 |
| TW200514772A (en) | 2005-05-01 |
| ZA200408423B (en) | 2005-10-11 |
| US20060009497A1 (en) | 2006-01-12 |
| CL2003002043A1 (es) | 2005-01-28 |
| RU2005102002A (ru) | 2005-09-20 |
| EP1519920A1 (en) | 2005-04-06 |
| WO2004002957A1 (en) | 2004-01-08 |
| AU2003229746A1 (en) | 2004-01-19 |
| CN1662498A (zh) | 2005-08-31 |
| JP2005532371A (ja) | 2005-10-27 |
| CA2490138A1 (en) | 2004-01-08 |
| IL165887A0 (en) | 2006-01-15 |
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