ZA200605841B - Prolinylarylacetamides - Google Patents
Prolinylarylacetamides Download PDFInfo
- Publication number
- ZA200605841B ZA200605841B ZA200605841A ZA200605841A ZA200605841B ZA 200605841 B ZA200605841 B ZA 200605841B ZA 200605841 A ZA200605841 A ZA 200605841A ZA 200605841 A ZA200605841 A ZA 200605841A ZA 200605841 B ZA200605841 B ZA 200605841B
- Authority
- ZA
- South Africa
- Prior art keywords
- denotes
- hydroxypyrrolidine
- chlorophenyl
- solvates
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 23
- -1 2-(4-hydroxypiperidin-1-yl)- ethanoyl Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 108010074860 Factor Xa Proteins 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- 208000007536 Thrombosis Diseases 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 5
- 238000002399 angioplasty Methods 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 206010022562 Intermittent claudication Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 108010039209 Blood Coagulation Factors Proteins 0.000 claims description 3
- 102000015081 Blood Coagulation Factors Human genes 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 239000003114 blood coagulation factor Substances 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- FNLBMMCNIOCYRG-NHCUHLMSSA-N (2r,4r)-2-n-[4-[[2-(tert-butylamino)acetyl]-methylamino]phenyl]-1-n-(4-chlorophenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(N(C(=O)CNC(C)(C)C)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 FNLBMMCNIOCYRG-NHCUHLMSSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- FUYFVQGJIBPFPP-WOJBJXKFSA-N [2-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-n-methylanilino]-2-oxoethyl] acetate Chemical compound C1=CC(N(C(=O)COC(C)=O)C)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 FUYFVQGJIBPFPP-WOJBJXKFSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 108090000190 Thrombin Proteins 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 229960004072 thrombin Drugs 0.000 description 8
- 239000003146 anticoagulant agent Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940127219 anticoagulant drug Drugs 0.000 description 5
- 208000001435 Thromboembolism Diseases 0.000 description 4
- 230000002785 anti-thrombosis Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 150000003235 pyrrolidines Chemical class 0.000 description 4
- 208000009205 Tinnitus Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 231100000886 tinnitus Toxicity 0.000 description 3
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 description 2
- 108010048049 Factor IXa Proteins 0.000 description 2
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 2
- 102000009123 Fibrin Human genes 0.000 description 2
- 108010073385 Fibrin Proteins 0.000 description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 108010000499 Thromboplastin Proteins 0.000 description 2
- 102000002262 Thromboplastin Human genes 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229950003499 fibrin Drugs 0.000 description 2
- 230000014508 negative regulation of coagulation Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 206010002388 Angina unstable Diseases 0.000 description 1
- 200000000007 Arterial disease Diseases 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 208000021910 Cerebral Arterial disease Diseases 0.000 description 1
- 102100025841 Cholecystokinin Human genes 0.000 description 1
- 101800001982 Cholecystokinin Proteins 0.000 description 1
- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 description 1
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 description 1
- 108010014173 Factor X Proteins 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 description 1
- 102100021022 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010038563 Reocclusion Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
- 108050006955 Tissue-type plasminogen activator Proteins 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940107137 cholecystokinin Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 238000002406 microsurgery Methods 0.000 description 1
- 230000004784 molecular pathogenesis Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940021317 other blood product in atc Drugs 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10358814A DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605841B true ZA200605841B (en) | 2007-10-31 |
Family
ID=34683363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605841A ZA200605841B (en) | 2003-12-16 | 2006-07-14 | Prolinylarylacetamides |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7732481B2 (https=) |
| EP (1) | EP1697318B1 (https=) |
| JP (1) | JP4800969B2 (https=) |
| KR (1) | KR20060113729A (https=) |
| CN (1) | CN1894210A (https=) |
| AR (1) | AR046765A1 (https=) |
| AT (1) | ATE406350T1 (https=) |
| AU (1) | AU2004299197B2 (https=) |
| BR (1) | BRPI0417630A (https=) |
| CA (1) | CA2549589A1 (https=) |
| DE (2) | DE10358814A1 (https=) |
| ES (1) | ES2310772T3 (https=) |
| MX (1) | MXPA06006740A (https=) |
| RU (1) | RU2006125509A (https=) |
| WO (1) | WO2005058817A1 (https=) |
| ZA (1) | ZA200605841B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1818330A1 (de) | 2006-02-14 | 2007-08-15 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Prolinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| MY146623A (en) | 2006-05-16 | 2012-09-14 | Boehringer Ingelheim Int | Substituted prolinamides, manufacturing, and the use thereof as medicaments |
| WO2009000878A1 (en) * | 2007-06-28 | 2008-12-31 | Novartis Ag | Kallikrein 7 modulators |
| WO2011027888A1 (ja) * | 2009-09-07 | 2011-03-10 | 大日本住友製薬株式会社 | ジアミド－フェニル誘導体、またはその薬学的に許容される塩 |
| CN109761957B (zh) * | 2019-01-18 | 2020-05-19 | 西安交通大学 | 一种含有羟脯氨酸的化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| BRPI0408444A (pt) * | 2003-04-03 | 2006-04-04 | Merck Patent Gmbh | derivados de 1-n-(fenil)-2-n-(fenil) pirazolidina-1,2-dicarboxamida como inibidores de fator xa de coagulação para o tratamento de trombose |
| PL377633A1 (pl) * | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| DE102004014945A1 (de) * | 2004-03-26 | 2005-10-13 | Merck Patent Gmbh | Prolinylderivate |
-
2003
- 2003-12-16 DE DE10358814A patent/DE10358814A1/de not_active Withdrawn
-
2004
- 2004-11-26 AU AU2004299197A patent/AU2004299197B2/en not_active Ceased
- 2004-11-26 RU RU2006125509/04A patent/RU2006125509A/ru not_active Application Discontinuation
- 2004-11-26 US US10/583,094 patent/US7732481B2/en not_active Expired - Fee Related
- 2004-11-26 AT AT04820404T patent/ATE406350T1/de not_active IP Right Cessation
- 2004-11-26 JP JP2006544256A patent/JP4800969B2/ja not_active Expired - Fee Related
- 2004-11-26 MX MXPA06006740A patent/MXPA06006740A/es not_active Application Discontinuation
- 2004-11-26 KR KR1020067011704A patent/KR20060113729A/ko not_active Withdrawn
- 2004-11-26 WO PCT/EP2004/013509 patent/WO2005058817A1/de not_active Ceased
- 2004-11-26 CN CNA2004800376989A patent/CN1894210A/zh active Pending
- 2004-11-26 CA CA002549589A patent/CA2549589A1/en not_active Abandoned
- 2004-11-26 BR BRPI0417630-8A patent/BRPI0417630A/pt not_active Application Discontinuation
- 2004-11-26 ES ES04820404T patent/ES2310772T3/es not_active Expired - Lifetime
- 2004-11-26 DE DE502004007959T patent/DE502004007959D1/de not_active Expired - Lifetime
- 2004-11-26 EP EP04820404A patent/EP1697318B1/de not_active Expired - Lifetime
- 2004-12-15 AR ARP040104656A patent/AR046765A1/es unknown
-
2006
- 2006-07-14 ZA ZA200605841A patent/ZA200605841B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060113729A (ko) | 2006-11-02 |
| DE502004007959D1 (de) | 2008-10-09 |
| US7732481B2 (en) | 2010-06-08 |
| DE10358814A1 (de) | 2005-07-21 |
| JP4800969B2 (ja) | 2011-10-26 |
| CN1894210A (zh) | 2007-01-10 |
| AU2004299197B2 (en) | 2010-08-05 |
| EP1697318B1 (de) | 2008-08-27 |
| MXPA06006740A (es) | 2006-08-18 |
| US20070185189A1 (en) | 2007-08-09 |
| WO2005058817A1 (de) | 2005-06-30 |
| ATE406350T1 (de) | 2008-09-15 |
| JP2007513988A (ja) | 2007-05-31 |
| EP1697318A1 (de) | 2006-09-06 |
| AR046765A1 (es) | 2005-12-21 |
| RU2006125509A (ru) | 2008-01-27 |
| CA2549589A1 (en) | 2005-06-30 |
| ES2310772T3 (es) | 2009-01-16 |
| BRPI0417630A (pt) | 2007-03-27 |
| AU2004299197A1 (en) | 2005-06-30 |
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