ZA200406027B - Novel amino acid derivatives method for productionthereof and pharmaceutical compositions comprisin g said derivative - Google Patents
Novel amino acid derivatives method for productionthereof and pharmaceutical compositions comprisin g said derivative Download PDFInfo
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- ZA200406027B ZA200406027B ZA200406027A ZA200406027A ZA200406027B ZA 200406027 B ZA200406027 B ZA 200406027B ZA 200406027 A ZA200406027 A ZA 200406027A ZA 200406027 A ZA200406027 A ZA 200406027A ZA 200406027 B ZA200406027 B ZA 200406027B
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- linear
- amino
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- 238000000034 method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000003862 amino acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 230000003287 optical effect Effects 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- -1 amino, guanidino Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 238000010511 deprotection reaction Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 101800004937 Protein C Proteins 0.000 claims description 6
- 102100036546 Salivary acidic proline-rich phosphoprotein 1/2 Human genes 0.000 claims description 6
- 101800001700 Saposin-D Proteins 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229960000856 protein c Drugs 0.000 claims description 6
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000005897 peptide coupling reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 230000004064 dysfunction Effects 0.000 claims description 3
- 230000002008 hemorrhagic effect Effects 0.000 claims description 3
- 230000023597 hemostasis Effects 0.000 claims description 3
- 239000003805 procoagulant Substances 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000002785 anti-thrombosis Effects 0.000 claims description 2
- 239000000729 antidote Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- KPWRTKYQQJDVGV-MIJJZIGMSA-N n-[(4-carbamimidoylphenyl)methyl]-6-[[(2r)-2-(cyclohexylmethylsulfonylamino)-3-methylbutanoyl]amino]-5,7-dihydrocyclopenta[b]pyridine-6-carboxamide Chemical compound N([C@H](C(C)C)C(=O)NC1(CC2=NC=CC=C2C1)C(=O)NCC=1C=CC(=CC=1)C(N)=N)S(=O)(=O)CC1CCCCC1 KPWRTKYQQJDVGV-MIJJZIGMSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005751 substituted indanyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- UEWOKJCHBKCJBO-XMMPIXPASA-N 2-[[(2r)-1-[[2-[(4-carbamimidoylphenyl)methylcarbamoyl]-1,3-dihydroinden-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]amino]acetic acid Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)C1(NC(=O)[C@@H](CC2CCCCC2)NCC(O)=O)CC2=CC=CC=C2C1 UEWOKJCHBKCJBO-XMMPIXPASA-N 0.000 claims 1
- 101100182248 Caenorhabditis elegans lat-2 gene Proteins 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- MBFKVZWVWIHPAS-AREMUKBSSA-N ethyl 2-[[(1r)-1-cyclohexyl-2-[[2-[[4-(n'-hydroxycarbamimidoyl)phenyl]methylcarbamoyl]-1,3-dihydroinden-2-yl]amino]-2-oxoethyl]amino]acetate Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)NC2(CC3=CC=CC=C3C2)C(=O)NCC=2C=CC(=CC=2)C(N)=NO)CCCCC1 MBFKVZWVWIHPAS-AREMUKBSSA-N 0.000 claims 1
- HNTLHUHETWTSBG-AREMUKBSSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[[(2r)-2-(cyclohexylmethylsulfonylamino)-3-methylbutanoyl]amino]-1,3-dihydroindene-2-carboxamide Chemical compound N([C@H](C(C)C)C(=O)NC1(CC2=CC=CC=C2C1)C(=O)NCC=1C=CC(=CC=1)C(N)=N)S(=O)(=O)CC1CCCCC1 HNTLHUHETWTSBG-AREMUKBSSA-N 0.000 claims 1
- DAJZUUWMNPOUMH-GDLZYMKVSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[[(2r)-2-cyclohexyl-2-(cyclohexylmethylsulfonylamino)acetyl]amino]-1,3-dihydroindene-2-carboxamide Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)C1(NC(=O)[C@H](NS(=O)(=O)CC2CCCCC2)C2CCCCC2)CC2=CC=CC=C2C1 DAJZUUWMNPOUMH-GDLZYMKVSA-N 0.000 claims 1
- ODLMIYJIJMWSNL-HSZRJFAPSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[[(2r)-3-methyl-2-(2-methylpropylsulfonylamino)butanoyl]amino]-1,3-dihydroindene-2-carboxamide Chemical compound C1C2=CC=CC=C2CC1(NC(=O)[C@@H](C(C)C)NS(=O)(=O)CC(C)C)C(=O)NCC1=CC=C(C(N)=N)C=C1 ODLMIYJIJMWSNL-HSZRJFAPSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 201000003542 Factor VIII deficiency Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 108010022999 Serine Proteases Proteins 0.000 description 2
- 102000012479 Serine Proteases Human genes 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 208000027276 Von Willebrand disease Diseases 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- 208000009429 hemophilia B Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 208000012137 von Willebrand disease (hereditary or acquired) Diseases 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010061932 Factor VIIIa Proteins 0.000 description 1
- 108010074105 Factor Va Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 108010079274 Thrombomodulin Proteins 0.000 description 1
- 102000012607 Thrombomodulin Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000006225 natural substrate Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- 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
- C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/10—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/28—Phenalenes; Hydrogenated phenalenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0202199A FR2836143B1 (fr) | 2002-02-21 | 2002-02-21 | Nouveaux derives d'acides amines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200406027B true ZA200406027B (en) | 2006-06-28 |
Family
ID=27636380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200406027A ZA200406027B (en) | 2002-02-21 | 2004-07-28 | Novel amino acid derivatives method for productionthereof and pharmaceutical compositions comprisin g said derivative |
Country Status (21)
Country | Link |
---|---|
US (1) | US7265220B2 (zh) |
EP (1) | EP1476421A2 (zh) |
JP (1) | JP4106337B2 (zh) |
KR (1) | KR100668194B1 (zh) |
CN (1) | CN1257889C (zh) |
AR (1) | AR038443A1 (zh) |
AU (1) | AU2003224198A1 (zh) |
BR (1) | BR0307776A (zh) |
CA (1) | CA2474785A1 (zh) |
EA (1) | EA006389B1 (zh) |
FR (1) | FR2836143B1 (zh) |
GE (1) | GEP20074100B (zh) |
HK (1) | HK1079764A1 (zh) |
MA (1) | MA27110A1 (zh) |
MX (1) | MXPA04007988A (zh) |
NO (1) | NO20043910L (zh) |
NZ (1) | NZ534359A (zh) |
PL (1) | PL370817A1 (zh) |
UA (1) | UA77763C2 (zh) |
WO (1) | WO2003070690A2 (zh) |
ZA (1) | ZA200406027B (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7592461B2 (en) * | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
GB0807828D0 (en) * | 2008-04-29 | 2008-06-04 | Vantia Ltd | Aminopyridine derivatives |
US9290485B2 (en) * | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
GB201322091D0 (en) | 2013-12-13 | 2014-01-29 | Cambridge Entpr Ltd | Modified serpins for the treatment of bleeding disorders |
EP3749697A4 (en) | 2018-02-05 | 2021-11-03 | Bio-Rad Laboratories, Inc. | CHROMATOGRAPHIC RESIN WITH A LIGAND WITH ANION EXCHANGE-HYDROPHOBIC MIXED MODE |
WO2020092139A1 (en) * | 2018-10-29 | 2020-05-07 | Huahai Us Inc. | Novel dipeptide compounds and uses thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2128186C1 (ru) | 1993-04-28 | 1999-03-27 | Кумиай Кемикал Индастри Ко., Лтд. | Производные амидов аминокислот, способ получения, фунгицидная композиция для сельского хозяйства и садоводства |
EP1007078A4 (en) * | 1996-11-19 | 2002-11-13 | Saulius Butenas | PEPTIDOMIMETIC COMPOUNDS CONTAINING A 6-PEPTIDYLAMINO-1-NAPHTALENESULFONAMIDE GROUP |
US6358960B1 (en) * | 1998-02-17 | 2002-03-19 | Ono Pharmaceutical Co., Ltd. | Amidino derivatives and drugs containing the same as the active ingredient |
-
2002
- 2002-02-21 FR FR0202199A patent/FR2836143B1/fr not_active Expired - Fee Related
-
2003
- 2003-02-17 CN CNB038041189A patent/CN1257889C/zh not_active Expired - Fee Related
- 2003-02-17 AU AU2003224198A patent/AU2003224198A1/en not_active Abandoned
- 2003-02-17 MX MXPA04007988A patent/MXPA04007988A/es active IP Right Grant
- 2003-02-17 JP JP2003569599A patent/JP4106337B2/ja not_active Expired - Fee Related
- 2003-02-17 US US10/505,005 patent/US7265220B2/en not_active Expired - Fee Related
- 2003-02-17 KR KR1020047013041A patent/KR100668194B1/ko not_active IP Right Cessation
- 2003-02-17 BR BR0307776-4A patent/BR0307776A/pt not_active IP Right Cessation
- 2003-02-17 WO PCT/FR2003/000506 patent/WO2003070690A2/fr active IP Right Grant
- 2003-02-17 GE GEAP8409A patent/GEP20074100B/en unknown
- 2003-02-17 EA EA200401011A patent/EA006389B1/ru not_active IP Right Cessation
- 2003-02-17 NZ NZ534359A patent/NZ534359A/en unknown
- 2003-02-17 PL PL03370817A patent/PL370817A1/xx not_active Application Discontinuation
- 2003-02-17 CA CA002474785A patent/CA2474785A1/fr not_active Abandoned
- 2003-02-17 EP EP03720618A patent/EP1476421A2/fr not_active Withdrawn
- 2003-02-17 UA UA20040907682A patent/UA77763C2/uk unknown
- 2003-02-21 AR ARP030100563A patent/AR038443A1/es not_active Application Discontinuation
-
2004
- 2004-07-28 ZA ZA200406027A patent/ZA200406027B/en unknown
- 2004-09-20 NO NO20043910A patent/NO20043910L/no not_active Application Discontinuation
- 2004-09-20 MA MA27865A patent/MA27110A1/fr unknown
-
2005
- 2005-12-22 HK HK05111846A patent/HK1079764A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HK1079764A1 (en) | 2006-04-13 |
MA27110A1 (fr) | 2004-12-20 |
CA2474785A1 (fr) | 2003-08-28 |
FR2836143B1 (fr) | 2004-04-16 |
EP1476421A2 (fr) | 2004-11-17 |
GEP20074100B (en) | 2007-05-10 |
KR20040085219A (ko) | 2004-10-07 |
EA200401011A1 (ru) | 2004-12-30 |
JP2005517734A (ja) | 2005-06-16 |
UA77763C2 (en) | 2007-01-15 |
MXPA04007988A (es) | 2004-11-26 |
US7265220B2 (en) | 2007-09-04 |
AR038443A1 (es) | 2005-01-12 |
EA006389B1 (ru) | 2005-12-29 |
NZ534359A (en) | 2005-12-23 |
CN1257889C (zh) | 2006-05-31 |
BR0307776A (pt) | 2004-12-07 |
NO20043910L (no) | 2004-09-20 |
WO2003070690A2 (fr) | 2003-08-28 |
AU2003224198A1 (en) | 2003-09-09 |
CN1633412A (zh) | 2005-06-29 |
JP4106337B2 (ja) | 2008-06-25 |
US20050085517A1 (en) | 2005-04-21 |
FR2836143A1 (fr) | 2003-08-22 |
PL370817A1 (en) | 2005-05-30 |
KR100668194B1 (ko) | 2007-01-11 |
WO2003070690A3 (fr) | 2004-04-08 |
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