NL8003580A - Nieuwe enkafalinederivaten. - Google Patents

Nieuwe enkafalinederivaten. Download PDF

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Publication number: NL8003580A
Authority: NL; Netherlands
Prior art keywords: group; formula; hydrogen; compound; straight
Prior art date: 1979-06-21

Application number

NL8003580A

Other languages

English (en)

Dutch (nl)

Original Assignee

Richardson Merrell Inc

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.)

1979-06-21

Filing date

1980-06-20

Publication date

1980-12-23

1980-06-20 Application filed by Richardson Merrell Inc filed Critical Richardson Merrell Inc

1980-12-23 Publication of NL8003580A publication Critical patent/NL8003580A/nl

Links

150000001875 compounds Chemical class 0.000 claims description 313
-1 methylene, carbonyl Chemical group 0.000 claims description 131
229910052739 hydrogen Inorganic materials 0.000 claims description 98
239000001257 hydrogen Substances 0.000 claims description 98
238000000034 method Methods 0.000 claims description 74
125000000217 alkyl group Chemical group 0.000 claims description 59
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
239000000203 mixture Substances 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 35
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
150000002367 halogens Chemical class 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
230000000903 blocking effect Effects 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 24
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 21
150000004702 methyl esters Chemical class 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
239000003153 chemical reaction reagent Substances 0.000 claims description 19
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 18
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 17
239000002585 base Substances 0.000 claims description 15
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
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125000001309 chloro group Chemical group Cl* 0.000 claims description 2
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125000000623 heterocyclic group Chemical group 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
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239000003638 chemical reducing agent Substances 0.000 claims 1
XLYOFNOQVPJJNP-DYCDLGHISA-N deuterium hydrogen oxide Chemical group [2H]O XLYOFNOQVPJJNP-DYCDLGHISA-N 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
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239000000243 solution Substances 0.000 description 69
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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150000002148 esters Chemical group 0.000 description 21
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
239000000706 filtrate Substances 0.000 description 19
239000000047 product Substances 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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239000003921 oil Substances 0.000 description 18
235000019198 oils Nutrition 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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238000001914 filtration Methods 0.000 description 14
238000003756 stirring Methods 0.000 description 14
238000001704 evaporation Methods 0.000 description 13
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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230000008020 evaporation Effects 0.000 description 12
150000002576 ketones Chemical class 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
OEBIVOHKFYSBPE-UHFFFAOYSA-N 4-Benzyloxybenzyl alcohol Chemical compound C1=CC(CO)=CC=C1OCC1=CC=CC=C1 OEBIVOHKFYSBPE-UHFFFAOYSA-N 0.000 description 11
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235000017557 sodium bicarbonate Nutrition 0.000 description 11
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238000010561 standard procedure Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000002274 desiccant Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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125000003118 aryl group Chemical group 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
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238000010168 coupling process Methods 0.000 description 8
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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 6
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OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
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YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical group [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 description 1
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NAHHXBZJUSLYIP-UHFFFAOYSA-N acetic acid;piperazin-2-one Chemical compound CC(O)=O.O=C1CNCCN1 NAHHXBZJUSLYIP-UHFFFAOYSA-N 0.000 description 1
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SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
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238000004090 dissolution Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
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SWVMLNPDTIFDDY-UHFFFAOYSA-N hydron;methyl 2-amino-3-phenylpropanoate;chloride Chemical compound Cl.COC(=O)C(N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-UHFFFAOYSA-N 0.000 description 1
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
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150000003951 lactams Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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235000019359 magnesium stearate Nutrition 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
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NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical class CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000017854 proteolysis Effects 0.000 description 1
230000037047 psychomotor activity Effects 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
239000002516 radical scavenger Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006476 reductive cyclization reaction Methods 0.000 description 1
230000001172 regenerating effect Effects 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
238000007363 ring formation reaction Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
230000007017 scission Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229920000260 silastic Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 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
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
108010005352 tert-butyloxycarbonyl-glycylphenylalanine Proteins 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- 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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring 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
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

NL8003580A 1979-06-21 1980-06-20 Nieuwe enkafalinederivaten. NL8003580A (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US5095079A	1979-06-21	1979-06-21
US5095079		1979-06-21
US13043180		1980-03-14
US06/130,431 US4341698A (en)	1979-06-21	1980-03-14	Enkaphalin derivatives
AU91877/82A AU559278B2 (en)	1979-06-21	1982-12-24	Piperazines
AU9187782		1982-12-24

Publications (1)

Publication Number	Publication Date
NL8003580A true NL8003580A (nl)	1980-12-23

Family

ID=36764304

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8003580A NL8003580A (nl)	1979-06-21	1980-06-20	Nieuwe enkafalinederivaten.

Country Status (17)

Country	Link
US (1)	US4341698A (it)
AU (1)	AU559278B2 (it)
CA (1)	CA1161838A (it)
CH (2)	CH648835A5 (it)
DE (1)	DE3022401A1 (it)
DK (1)	DK265780A (it)
ES (1)	ES492566A0 (it)
FR (2)	FR2459236A1 (it)
GB (3)	GB2051821B (it)
IE (1)	IE49834B1 (it)
IL (1)	IL60245A (it)
IT (1)	IT1148277B (it)
NL (1)	NL8003580A (it)
NO (1)	NO801855L (it)
NZ (1)	NZ193934A (it)
PH (1)	PH19222A (it)
SE (3)	SE447250B (it)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6369080B2 (en)	1996-10-11	2002-04-09	Cor Therapeutics, Inc.	Selective factor Xa inhibitors
US6194435B1 (en)	1996-10-11	2001-02-27	Cor Therapeutics, Inc.	Lactams as selective factor Xa inhibitors
US6063794A (en)	1996-10-11	2000-05-16	Cor Therapeutics Inc.	Selective factor Xa inhibitors
US6262047B1 (en)	1996-10-11	2001-07-17	Cor Therapeutics, Inc.	Selective factor Xa inhibitors
WO1998046628A1 (en) *	1997-04-14	1998-10-22	Cor Therapeutics, Inc.	SELECTIVE FACTOR Xa INHIBITORS
AU6896298A (en)	1997-04-14	1998-11-11	Cor Therapeutics, Inc.	Selective factor xa inhibitors
US6369063B1 (en)	1997-04-14	2002-04-09	Cor Therapeutics, Inc.	Selective factor Xa inhibitors
US6228854B1 (en)	1997-08-11	2001-05-08	Cor Therapeutics, Inc.	Selective factor Xa inhibitors
US6333321B1 (en)	1997-08-11	2001-12-25	Cor Therapeutics, Inc.	Selective factor Xa inhibitors
US6218382B1 (en)	1997-08-11	2001-04-17	Cor Therapeutics, Inc	Selective factor Xa inhibitors
WO2006102283A2 (en)	2005-03-22	2006-09-28	Azevan Pharmaceuticals, Inc.	Beta-lactamylalkanoic acids for treating premenstrual disorders
EP1910346B1 (en)	2005-07-19	2019-02-27	Azevan Pharmaceuticals, Inc.	Beta-lactamyl phenylalanine, cysteine, and serine vasopressin antagonist
CA2647143A1 (en) *	2006-03-30	2007-10-11	Palatin Technologies, Inc.	Cyclic natriuretic peptide constructs
ATE539762T1 (de) *	2006-03-30	2012-01-15	Palatin Technologies Inc	Aminosäureersatz für peptidkonstruktionen
US8114844B2 (en) *	2006-03-30	2012-02-14	Palatin Technologies, Inc.	Linear and cyclic melanocortin receptor-specific peptidomimetics
EP2004633A4 (en) *	2006-03-30	2009-08-26	Palatin Technologies Inc	LINEAR NATRIURETIC PEPTIDE CONSTRUCTS
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1980
- 1980-03-14 US US06/130,431 patent/US4341698A/en not_active Expired - Lifetime
- 1980-06-04 CA CA000353383A patent/CA1161838A/en not_active Expired
- 1980-06-04 NZ NZ193934A patent/NZ193934A/xx unknown
- 1980-06-04 IE IE1152/80A patent/IE49834B1/en not_active IP Right Cessation
- 1980-06-06 SE SE8004254A patent/SE447250B/sv not_active IP Right Cessation
- 1980-06-06 IL IL60245A patent/IL60245A/xx unknown
- 1980-06-14 DE DE19803022401 patent/DE3022401A1/de not_active Withdrawn
- 1980-06-16 PH PH24144A patent/PH19222A/en unknown
- 1980-06-17 CH CH1248/84A patent/CH648835A5/de not_active IP Right Cessation
- 1980-06-17 CH CH469880A patent/CH645363A5/de not_active IP Right Cessation
- 1980-06-18 ES ES492566A patent/ES492566A0/es active Granted
- 1980-06-18 GB GB8019903A patent/GB2051821B/en not_active Expired
- 1980-06-20 NL NL8003580A patent/NL8003580A/nl not_active Application Discontinuation
- 1980-06-20 DK DK265780A patent/DK265780A/da not_active Application Discontinuation
- 1980-06-20 FR FR8013795A patent/FR2459236A1/fr active Granted
- 1980-06-20 NO NO801855A patent/NO801855L/no unknown
- 1980-06-20 IT IT49032/80A patent/IT1148277B/it active
1981
- 1981-02-04 FR FR8102171A patent/FR2473042A1/fr active Granted
1982
- 1982-09-10 GB GB08225842A patent/GB2106515B/en not_active Expired
- 1982-09-10 GB GB08225828A patent/GB2132605B/en not_active Expired
- 1982-12-24 AU AU91877/82A patent/AU559278B2/en not_active Ceased
1985
- 1985-02-22 SE SE8500878A patent/SE460541B/sv not_active IP Right Cessation
- 1985-02-22 SE SE8500877A patent/SE460540B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH648835A5 (de)	1985-04-15
GB2132605B (en)	1985-01-03
SE460541B (sv)	1989-10-23
GB2106515A (en)	1983-04-13
FR2459236B1 (it)	1984-01-06
DK265780A (da)	1980-12-22
GB2051821B (en)	1983-04-27
GB2051821A (en)	1981-01-21
IL60245A (en)	1985-08-30
DE3022401A1 (de)	1981-01-08
GB2132605A (en)	1984-07-11
SE8004254L (sv)	1980-12-22
FR2473042B1 (it)	1983-07-01
SE447250B (sv)	1986-11-03
IE49834B1 (en)	1985-12-25
US4341698A (en)	1982-07-27
NZ193934A (en)	1983-02-15
CA1161838A (en)	1984-02-07
CH645363A5 (de)	1984-09-28
NO801855L (no)	1980-12-22
SE8500878D0 (sv)	1985-02-22
SE8500877D0 (sv)	1985-02-22
IE801152L (en)	1980-12-21
AU9187782A (en)	1983-04-21
IT8049032A0 (it)	1980-06-20
FR2473042A1 (fr)	1981-07-10
IT1148277B (it)	1986-11-26
ES8105720A1 (es)	1981-06-16
FR2459236A1 (fr)	1981-01-09
AU559278B2 (en)	1987-03-05
SE460540B (sv)	1989-10-23
PH19222A (en)	1986-02-12
GB2106515B (en)	1983-11-23
ES492566A0 (es)	1981-06-16
SE8500877L (sv)	1985-02-22

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1987-07-01	BA	A request for search or an international-type search has been filed
1987-08-03	BB	A search report has been drawn up
1988-01-04	BC	A request for examination has been filed
1995-02-01	BV	The patent application has lapsed

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AU2001264977B2 (en)	2005-04-14	Melanocortin receptor agonists
AU766191B2 (en)	2003-10-09	Substituted piperidines as melanocortin-4 receptor agonists
AU2010295461B2 (en)	2016-03-03	Process for preparing azabicyclic compounds
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JP2003528088A (ja)	2003-09-24	メラノコルチン受容体作働薬としての置換ピペリジン類
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AU2002327172B2 (en)	2007-11-15	Substituted 1-benzazepines and derivatives thereof
IE55872B1 (en)	1991-02-14	Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives
EP1055683A1 (en)	2000-11-29	Novel acetamide derivative and use thereof
US5484917A (en)	1996-01-16	Substituted tetrahydrobenzazepinones
FR2467845A1 (fr)	1981-04-30	Nouveaux derives mercapto-acyles de prolines 4,4-disubstituees et de dehydroprolines 4-substituees, utiles notamment comme medicaments hypotenseurs, compositions therapeutiques et formes pharmaceutiques les contenant, et intermediaires utiles pour leur synthese
HUT70148A (en)	1995-09-28	Isoquinolone derivatives as techykinin receptor antagonists, process for producing thereof and pharmaceutical compositions comprising them
NZ259398A (en)	1996-02-27	N-(aminoacetyl) pyrrolidine derivatives and pharmaceutical compositions thereof
US4483988A (en)	1984-11-20	Substituted derivatives of 4-t-alkoxycarbonyl-piperazin-2-ones
US4435571A (en)	1984-03-06	5-(Substituted benzyl)-6-oxo-2-piperazine carboxylic acids and esters
JPH07121908B2 (ja)	1995-12-25	新規置換アミノ酸誘導体、その製法およびそれを含有する医薬組成物
JPH0331719B2 (it)	1991-05-08
EP0186431B1 (en)	1988-02-03	Anti-hypertensive octahydro-6-azaindole dipeptide derivatives