SK15662001A3 - Nové zlúčeniny - Google Patents

Nové zlúčeniny Download PDF

Info

Publication number: SK15662001A3
Authority: SK; Slovakia
Prior art keywords: group; amino; compound; tert; formula
Prior art date: 1999-05-03

Application number

SK1566-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Marcel Linschoten

Magnus Polla

Original Assignee

Astrazeneca Ab

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.)

1999-05-03

Filing date

2000-05-03

Publication date

2002-09-10

2000-05-03 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2002-09-10 Publication of SK15662001A3 publication Critical patent/SK15662001A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 146
150000003839 salts Chemical class 0.000 claims abstract description 42
239000012453 solvate Substances 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 32
108090000201 Carboxypeptidase B2 Proteins 0.000 claims abstract description 24
102000003847 Carboxypeptidase B2 Human genes 0.000 claims abstract description 23
238000002360 preparation method Methods 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
230000008569 process Effects 0.000 claims abstract description 11
238000011282 treatment Methods 0.000 claims abstract description 11
239000004480 active ingredient Substances 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 3
-1 amino, amidino Chemical group 0.000 claims description 76
239000000203 mixture Substances 0.000 claims description 62
125000000623 heterocyclic group Chemical group 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 33
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 14
239000003112 inhibitor Substances 0.000 claims description 13
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
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239000003153 chemical reaction reagent Substances 0.000 claims description 9
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229910052801 chlorine Inorganic materials 0.000 claims description 8
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238000011321 prophylaxis Methods 0.000 claims description 8
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239000003146 anticoagulant agent Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
125000003435 aroyl group Chemical group 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 5
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125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000005239 aroylamino group Chemical group 0.000 claims description 5
125000005110 aryl thio group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 5
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125000003545 alkoxy group Chemical group 0.000 claims description 4
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239000002319 fibrinogen receptor antagonist Substances 0.000 claims description 4
230000007246 mechanism Effects 0.000 claims description 4
230000010534 mechanism of action Effects 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 2
239000005557 antagonist Substances 0.000 claims description 2
230000008878 coupling Effects 0.000 claims description 2
238000010168 coupling process Methods 0.000 claims description 2
238000005859 coupling reaction Methods 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
150000003536 tetrazoles Chemical class 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims 7
108090000364 Ligases Proteins 0.000 claims 3
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229960001123 epoprostenol Drugs 0.000 claims 3
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238000005481 NMR spectroscopy Methods 0.000 description 23
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239000012267 brine Substances 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
239000012074 organic phase Substances 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
239000000460 chlorine Substances 0.000 description 13
239000012043 crude product Substances 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
239000012044 organic layer Substances 0.000 description 11
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
230000020764 fibrinolysis Effects 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
102000013566 Plasminogen Human genes 0.000 description 6
108010051456 Plasminogen Proteins 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
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235000019322 gelatine Nutrition 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
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125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
230000002792 vascular Effects 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
XGFNIBFPQHGAQO-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]methyl]-3-[6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridin-3-yl]propanoic acid Chemical compound C1=NC(NC(=O)OC(C)(C)C)=CC=C1CC(C(O)=O)CP(O)(=O)CCCC1=CC=CC=C1 XGFNIBFPQHGAQO-UHFFFAOYSA-N 0.000 description 4
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
108010073863 saruplase Proteins 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
MAKMAMVHNXFPEY-UHFFFAOYSA-N tert-butyl 4-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCC1C(=O)OC(C)(C)OC1=O MAKMAMVHNXFPEY-UHFFFAOYSA-N 0.000 description 1
WZROBBWIJBBWQP-UHFFFAOYSA-N tert-butyl n-(5-formylpyridin-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=O)C=N1 WZROBBWIJBBWQP-UHFFFAOYSA-N 0.000 description 1
WWIMVFCGNYLUMJ-UHFFFAOYSA-N tert-butyl n-[4-(hydroxymethyl)pyridin-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(CO)=CC=N1 WWIMVFCGNYLUMJ-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
229960000103 thrombolytic agent Drugs 0.000 description 1
230000002537 thrombolytic effect Effects 0.000 description 1
229960005001 ticlopidine Drugs 0.000 description 1
PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
229960000187 tissue plasminogen activator Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000007631 vascular surgery Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by 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
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
- A61K38/57—Protease inhibitors from animals; from humans
- 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
- A61K31/13—Amines
- A61K31/132—Amines having two or more amino groups, e.g. spermidine, putrescine
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Zoology (AREA)
Gastroenterology & Hepatology (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Peptides Or Proteins (AREA)

SK1566-2001A 1999-05-03 2000-05-03 Nové zlúčeniny SK15662001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9901572A SE9901572D0 (sv)	1999-05-03	1999-05-03	New compounds
PCT/SE2000/000846 WO2000066550A1 (en)	1999-05-03	2000-05-03	New compounds

Publications (1)

Publication Number	Publication Date
SK15662001A3 true SK15662001A3 (sk)	2002-09-10

Family

ID=20415425

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1566-2001A SK15662001A3 (sk)	1999-05-03	2000-05-03	Nové zlúčeniny

Country Status (23)

Country	Link
US (2)	US7354895B1 (zh)
EP (1)	EP1180099A1 (zh)
JP (1)	JP4270759B2 (zh)
KR (1)	KR20020010631A (zh)
CN (1)	CN1358187A (zh)
AR (1)	AR028826A1 (zh)
AU (1)	AU4447100A (zh)
BR (1)	BR0010256A (zh)
CA (1)	CA2371215A1 (zh)
CZ (1)	CZ20013931A3 (zh)
EE (1)	EE200100573A (zh)
HK (1)	HK1042493A1 (zh)
HU (1)	HUP0202379A3 (zh)
IL (1)	IL145953A0 (zh)
IS (1)	IS6141A (zh)
MX (1)	MXPA01011043A (zh)
NO (1)	NO20015374D0 (zh)
PL (1)	PL356140A1 (zh)
SE (1)	SE9901572D0 (zh)
SK (1)	SK15662001A3 (zh)
TR (1)	TR200103144T2 (zh)
WO (1)	WO2000066550A1 (zh)
ZA (2)	ZA200108966B (zh)

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MXPA02002671A (es)	1999-09-14	2002-07-30	Meiji Seika Kaisha	Derivado de acido fosfonico que tiene actividad inhibidora contra la carboxipeptidasa b.
PL361054A1 (en) *	2000-08-17	2004-09-20	Pfizer Inc.	Substituted imidazoles as tafia inhibitors
SE0103272D0 (sv)	2001-09-28	2001-09-28	Astrazeneca Ab	Chemical compounds
MXPA04005940A (es)	2002-01-22	2004-09-13	Pfizer	Acidos 3-(imidazolil)-2-aminopropanoicos.
WO2003061652A1 (en) *	2002-01-22	2003-07-31	Pfizer Limited	3-(imidazolyl)-2-alkoxypropanoic acids as tafia inhibitors
US6713496B2 (en)	2002-01-22	2004-03-30	Pfizer Inc	3-(imidazolyl)-2-alkoxypropanoic acids
KR100972717B1 (ko) *	2002-03-21	2010-07-27	바이엘 쉐링 파마 악티엔게젤샤프트	혈장 카르복시펩티드분해효소 ｂ 억제제
WO2010050525A1 (ja)	2008-10-29	2010-05-06	大正製薬株式会社	ＴＡＦＩａ阻害活性を有する化合物
US20220106335A1 (en) *	2019-02-08	2022-04-07	Astrazeneca Ab	Arginase inhibitors and methods of use thereof
CN111110837B (zh) *	2020-01-06	2022-11-25	中国人民解放军陆军军医大学	一种羧肽酶抑制剂在制备预防重症致死性轮状病毒感染药物中的应用

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US2516307A (en) *	1949-01-06	1950-07-25	Gen Mills Inc	Vinyl resins plasticized with cyano esters
US4560680A (en) *	1982-03-15	1985-12-24	E. R. Squibb & Sons, Inc.	Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors
US4849414A (en) *	1986-06-11	1989-07-18	E. R. Squibb & Sons, Inc.	Substituted aminoalkanoylaminoalkyl phosphonate angiotensin converting enzyme inhibitors
FR2610951B1 (fr) *	1987-02-17	1989-05-05	Aerospatiale	Armature tissee pour materiau composite
IL86951A (en) *	1987-07-06	1996-07-23	Procter & Gamble Pharma	Methylene phosphonoalkylphosphinates and pharmaceutical preparations containing them
CZ282889B6 (cs) *	1991-12-17	1997-11-12	Procter And Gamble Pharmaceuticals, Inc.	Použití difosfonátů a parathormonu pro výrobu léčiva, které se používá pro léčení osteoporosy
US5550119A (en) *	1995-03-02	1996-08-27	Ciba-Geigy Corporation	Phosphono substituted tetrazole derivatives as ECE inhibitors
US5672592A (en) *	1996-06-17	1997-09-30	Guilford Pharmaceuticals Inc.	Certain phosphonomethyl-pentanedioic acid derivatives thereof
JP3440305B2 (ja) *	1997-04-02	2003-08-25	高砂香料工業株式会社	７−（ｎ−置換アミノ）−２−フェニルヘプタン酸エステル誘導体及び該誘導体の製造方法
DE69823019T2 (de)	1997-02-27	2005-03-31	Wyeth Holdings Corp.	N-hydroxy-2-(alkyl, aryl oder heteroaryl sulfanyl, sulfinyl oder sulfonyl)-3-substituierte alkyl-, aryl- oder heteroarylamide als matrixmetalloproteinaseinhibitoren
AR023819A1 (es) *	1999-05-03	2002-09-04	Astrazeneca Ab	FORMULACIoN FARMACEUTICA, KIT DE PARTES Y UTILIZACION DE DICHA FORMULACION
SE9901573D0 (sv) *	1999-05-03	1999-05-03	Astra Ab	New compounds
MXPA02002671A (es) *	1999-09-14	2002-07-30	Meiji Seika Kaisha	Derivado de acido fosfonico que tiene actividad inhibidora contra la carboxipeptidasa b.

1999
- 1999-05-03 SE SE9901572A patent/SE9901572D0/xx unknown
2000
- 2000-04-28 AR ARP000102082A patent/AR028826A1/es not_active Application Discontinuation
- 2000-05-03 CN CN00809484A patent/CN1358187A/zh active Pending
- 2000-05-03 KR KR1020017014014A patent/KR20020010631A/ko not_active Withdrawn
- 2000-05-03 MX MXPA01011043A patent/MXPA01011043A/es unknown
- 2000-05-03 JP JP2000615381A patent/JP4270759B2/ja not_active Expired - Fee Related
- 2000-05-03 AU AU44471/00A patent/AU4447100A/en not_active Abandoned
- 2000-05-03 CA CA002371215A patent/CA2371215A1/en not_active Abandoned
- 2000-05-03 US US09/600,660 patent/US7354895B1/en not_active Expired - Fee Related
- 2000-05-03 HK HK02104304.1A patent/HK1042493A1/zh unknown
- 2000-05-03 HU HU0202379A patent/HUP0202379A3/hu unknown
- 2000-05-03 IL IL14595300A patent/IL145953A0/xx unknown
- 2000-05-03 TR TR2001/03144T patent/TR200103144T2/xx unknown
- 2000-05-03 EP EP00925844A patent/EP1180099A1/en not_active Ceased
- 2000-05-03 SK SK1566-2001A patent/SK15662001A3/sk unknown
- 2000-05-03 WO PCT/SE2000/000846 patent/WO2000066550A1/en not_active Application Discontinuation
- 2000-05-03 CZ CZ20013931A patent/CZ20013931A3/cs unknown
- 2000-05-03 PL PL00356140A patent/PL356140A1/xx not_active Application Discontinuation
- 2000-05-03 BR BR0010256-3A patent/BR0010256A/pt not_active Application Discontinuation
- 2000-05-03 EE EEP200100573A patent/EE200100573A/xx unknown
2001
- 2001-10-30 ZA ZA200108966A patent/ZA200108966B/en unknown
- 2001-10-30 ZA ZA200108967A patent/ZA200108967B/en unknown
- 2001-11-01 IS IS6141A patent/IS6141A/is unknown
- 2001-11-02 NO NO20015374A patent/NO20015374D0/no not_active Application Discontinuation
2005
- 2005-12-02 US US11/293,060 patent/US7423012B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PL356140A1 (en)	2004-06-14
HK1042493A1 (zh)	2002-08-16
MXPA01011043A (es)	2002-06-04
US7423012B2 (en)	2008-09-09
WO2000066550A8 (en)	2001-01-25
JP2002543179A (ja)	2002-12-17
ZA200108966B (en)	2003-01-30
US7354895B1 (en)	2008-04-08
NO20015374L (no)	2001-11-02
HUP0202379A3 (en)	2003-04-28
CZ20013931A3 (cs)	2002-04-17
EP1180099A1 (en)	2002-02-20
KR20020010631A (ko)	2002-02-04
AU4447100A (en)	2000-11-17
NO20015374D0 (no)	2001-11-02
CA2371215A1 (en)	2000-11-09
WO2000066550A1 (en)	2000-11-09
CN1358187A (zh)	2002-07-10
ZA200108967B (en)	2003-01-30
AR028826A1 (es)	2003-05-28
EE200100573A (et)	2003-02-17
IL145953A0 (en)	2002-11-10
IS6141A (is)	2001-11-01
JP4270759B2 (ja)	2009-06-03
TR200103144T2 (tr)	2004-11-22
SE9901572D0 (sv)	1999-05-03
US20060079484A1 (en)	2006-04-13
HUP0202379A2 (hu)	2002-12-28
BR0010256A (pt)	2002-02-13

Publication	Publication Date	Title
US7071175B1 (en)	2006-07-04	Pyridine mercapto carboxylic acids as carboxypeptidase U inhibitors
US5736521A (en)	1998-04-07	Method of treatment and prophylaxis of arterial thrombosis
AU2006235835B2 (en)	2009-06-25	Non-covalent inhibitors of urokinase and blood vessel formation
EP0910573B1 (en)	2003-01-29	New amino acid derivatives and their use as thrombin inhibitors
US20090012087A1 (en)	2009-01-08	New Aza-Bicyclohexane Compounds Useful As Inhibitors Of Thrombin
KR100347646B1 (ko)	2002-12-05	매트릭스메탈로프로테아제억제제
SK15662001A3 (sk)	2002-09-10	Nové zlúčeniny
RU2248359C2 (ru)	2005-03-20	Ингибиторы фактора viia
EP0322633B1 (en)	1991-05-22	Mercapto-acylamino acid antihypertensives
CZ20002070A3 (cs)	2001-01-17	Nové sloučeniny