HRP20220264T1 - Proces za pripremanje n-((1r,2s,sr)-5-(terc-butilamino)-2-((s)-3-(7-terc-butilpirazolo[1,5-a][1,3,5]triazin-4-ilamino)-2-oksopirolidin-1-il)cikloheksil)acetamida - Google Patents
Proces za pripremanje n-((1r,2s,sr)-5-(terc-butilamino)-2-((s)-3-(7-terc-butilpirazolo[1,5-a][1,3,5]triazin-4-ilamino)-2-oksopirolidin-1-il)cikloheksil)acetamida Download PDFInfo
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- HRP20220264T1 HRP20220264T1 HRP20220264TT HRP20220264T HRP20220264T1 HR P20220264 T1 HRP20220264 T1 HR P20220264T1 HR P20220264T T HRP20220264T T HR P20220264TT HR P20220264 T HRP20220264 T HR P20220264T HR P20220264 T1 HRP20220264 T1 HR P20220264T1
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- 238000000034 method Methods 0.000 title claims 22
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- 239000002253 acid Substances 0.000 claims 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 8
- 239000011877 solvent mixture Substances 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 5
- 238000006268 reductive amination reaction Methods 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000004678 hydrides Chemical class 0.000 claims 3
- 150000007517 lewis acids Chemical class 0.000 claims 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 claims 2
- 229910017912 NH2OH Inorganic materials 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229940125773 compound 10 Drugs 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 2
- 239000004210 ether based solvent Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- -1 sodium triacetoxyborohydride Chemical compound 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- 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
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- Chemical Kinetics & Catalysis (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (22)
1. Proces za pripremanje spoja I sa formulom
[image]
koji obuhvaća korake
a) reagiranja spoja 1 sa formulom
[image]
sa spojem 2 sa općom formulom
[image]
gdje R1 je odlazeća grupa i sa kiselinom, u odgovarajućem otapalu da se dobije spoj 3 sa formulom
[image]
b) reagiranja spoja 3 u reakciji reduktivne aminacije sa primarnim ili sekundarnim aminom (HNR2R3) gdje
R2 i R3 su vodik ili C1-C6 alkil;
posredovano Lewis-ovom kiselinom nakon čega slijedi reakcija sa odgovarajućim donorom hidrida ili kombinacijom katalizatora i plina vodika, da se dobije spoj 4 sa formulom
[image]
pri čemu X je neorganski ili organski kontra ion;
c) naknadnog reagiranja soli spoja 4 sa i-PrOH /H2SO4 ili oslobađanja baze prvo sa NaOH i zatim sa odgovarajućom smjesom kiselina/otapalo, da se dobije spoj 5 sa formulom
[image]
d) reagiranja spoja 5, ili njegove soli, u reduktivnoj aminaciji, u odgovarajućem otapalu i korištenjem izvora hidrida, sa spojem 6 sa formulom
[image]
da se dobije spoj 7 sa formulom,
[image]
e) koje zatim reagira sa kiselinom, u prisustvu NH2OH, ili njegove soli, i odgovarajućim otapalom da se dobije Spoj 8 sa formulom
[image]
f) koje dalje reagira sa kiselinom, bazom, i zagrijava se do 45 - 70 °C u odgovarajućem otapalu ili smjesi otapala da se dobije Spoj 9 sa formulom
[image]
g) naknadnog uklanjanja zaštitne grupe da se dobije Spoj 10 sa formulom
[image]
h) koje zatim reagira sa Spojem 11a sa formulom
[image]
gdje X je odlazeća grupa da se dobije spoj I, koje zatim kristalizira iz odgovarajuće smjese otapala.
2. Proces prema patentnom zahtjevu 1 pri čemu odlazeća grupa u koraku a) je halogen ili OAc odlazeća grupa.
3. Proces prema patentnom zahtjevu 1 pri čemu kiselina u koraku a) je mineralna ili organska kiselina.
4. Proces prema patentnom zahtjevu 3 pri čemu kiselina je metansulfonska kiselina (MSA) ili kamforsulfonska kiselina (CSA).
5. Proces prema patentnom zahtjevu 1 pri čemu kiselina u koraku a) je Lewis-ova kiselina.
6. Proces prema patentnom zahtjevu 5 pri čemu Lewis-ova kiselina je LiX, gdje X je halogen, ili BF3-etarat.
7. Proces prema patentnom zahtjevu 1 pri čemu otapalo u koraku a) je DCM, DCE, CHCl3, CCl4, dietil etar, THF, metil t-butil etar ili druga etarska otapala ili njihova smjese.
8. Proces prema patentnom zahtjevu 1 pri čemu spoj 4 je slobodna baza.
9. Proces prema patentnom zahtjevu 1 pri čemu spoj 4 je amonijeva sol.
10. Proces prema patentnom zahtjevu 1 pri čemu smeša kiselina/rastvarač u koraku c) je MSA/DCM u odnosu 1:21.4, ili H2SO4/IPA u odnosu 1:588.
11. Proces prema patentnom zahtjevu 1 pri čemu H2SO4 sol je formirana u koraku c).
12. Proces prema patentnom zahtjevu 1 pri čemu izvor hidrida u koraku d) je triacetoksiborohidrid.
13. Proces prema patentnom zahtjevu 1 pri čemu kiselina u koraku e) je TFA i otapalo je toluen.
14. Proces prema patentnom zahtjevu 1 pri čemu NH2OH je korišten u koraku e).
15. Proces prema patentnom zahtjevu 1 pri čemu je Spoj 8 reagirao sa kiselinom ili bazom.
16. Proces prema patentnom zahtjevu 1 pri čemu je Spoj 8 zagrijavano do 45 - 70 °C u smjesi otapalo/otapalo pri čemu su otapala toluen, izo-propil acetat, n-heptan, NMP, DMF, dietil etar, THF, metil t-butil etar ili druga etarska otapala.
17. Proces prema patentnom zahtjevu 1 pri čemu Spoj 9 je kristaliziran iz smjese otapala izo-propil acetat/n-heptan.
18. Proces prema patentnom zahtjevu 1 pri čemu reduktivna aminacija u koraku b) koristi Pd/C u MeOH ili Pt/Al u THF sa vodik gasom i reduktivna aminacija u koraku d) koristi natrij triacetoksiborohidrid.
19. Proces prema patentnom zahtjevu 1 pri čemu se HBr sol spoja 10 formira u koraku g).
20. Proces prema patentnom zahtjevu 1 pri čemu spoj 11 u koraku h) je aktiviran sa 1-metilimidazolom i difenil fosforil kloridom da se dobije spoj 11a
[image]
21. Proces prema patentnom zahtjevu 1 pri čemu spoj I u koraku h) kristalizira iz smjese otapala 2-MeTHF i n-heptana.
22. Spoj kao što je prikazan u tabeli ispod;
[image]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762534908P | 2017-07-20 | 2017-07-20 | |
| EP18785785.9A EP3655395B1 (en) | 2017-07-20 | 2018-07-19 | Process for the preparation of n-((1r,2s,sr)-5-(tert-butylamino)-2-((s)-3-(7-tert-butylpyrazolo[1,5-a][1,3,5]triazin-4-ylamino)-2-oxopyrrolidin-1-yl)cyclohexyl)acetamide |
| PCT/US2018/042797 WO2019018592A2 (en) | 2017-07-20 | 2018-07-19 | PROCESS FOR THE PREPARATION OF N- ((1R, 2S, 5R) -5- (TERT-BUTYLAMINO) -2 - ((S) -3- (7-TERT-BUTYLPYRAZOLO [1,5-A]] 1,3 , 5] triazin-4-ylamino) -2-oxopyrrolidin-1-yl) cyclohexyl) acetamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20220264T1 true HRP20220264T1 (hr) | 2022-05-13 |
| HRP20220264T8 HRP20220264T8 (hr) | 2022-05-27 |
Family
ID=63834628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220264TT HRP20220264T8 (hr) | 2017-07-20 | 2018-07-19 | Proces za pripremanje n-((1r,2s,sr)-5-(terc-butilamino)-2-((s)-3-(7-terc-butilpirazolo[1,5-a][1,3,5]triazin-4-ilamino)-2-oksopirolidin-1-il)cikloheksil)acetamida |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US11254679B2 (hr) |
| EP (1) | EP3655395B1 (hr) |
| JP (1) | JP2020527576A (hr) |
| KR (1) | KR20200031656A (hr) |
| CN (1) | CN110933946A (hr) |
| AU (1) | AU2018304290B2 (hr) |
| BR (1) | BR112020000418A2 (hr) |
| CA (1) | CA3070423A1 (hr) |
| CY (1) | CY1125023T1 (hr) |
| DK (1) | DK3655395T3 (hr) |
| EA (1) | EA202090346A1 (hr) |
| ES (1) | ES2907640T3 (hr) |
| HR (1) | HRP20220264T8 (hr) |
| HU (1) | HUE058049T2 (hr) |
| IL (2) | IL293088A (hr) |
| LT (1) | LT3655395T (hr) |
| PL (1) | PL3655395T3 (hr) |
| PT (1) | PT3655395T (hr) |
| RS (1) | RS62941B1 (hr) |
| SG (1) | SG11202000441QA (hr) |
| SI (1) | SI3655395T1 (hr) |
| WO (1) | WO2019018592A2 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112020014574A2 (pt) * | 2018-01-22 | 2020-12-08 | Bristol-Myers Squibb Company | Composições e métodos para o tratamento do câncer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1802378A (zh) * | 2003-05-30 | 2006-07-12 | (株)中外制药 | β－链模拟物及其相关方法 |
| US7629351B2 (en) * | 2006-07-28 | 2009-12-08 | Bristol-Myers Squibb Company | N-((1R,2S,5R)-5-(tert-butylamino)-2-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino) pyrrolidin-1-yl)cyclohexyl)acetamide and other modulators of chemokine receptor activity, crystalline forms and process |
| US7671062B2 (en) * | 2006-07-28 | 2010-03-02 | Bristol-Myers Squibb Company | Modulators of chemokine receptor activity, crystalline forms and process |
| CN100593536C (zh) * | 2007-01-09 | 2010-03-10 | 吉尔生化（上海）有限公司 | 一种n-芴甲氧羰基-n-三苯甲基-d-谷氨酰胺的合成法 |
| US8383812B2 (en) | 2009-10-13 | 2013-02-26 | Bristol-Myers Squibb Company | N-((1R,2S,5R)-5-(tert-butylamino)-2-((S)-3-(7-tert-butylpyrazolo[1,5-A][1,3,5]triazin-4-ylamino)-2-oxopyrrolidin-1-yl)cyclohexyl)acetamide, a dual modulator of chemokine receptor activity, crystalline forms and processes |
| WO2013100132A1 (ja) * | 2011-12-28 | 2013-07-04 | 中外製薬株式会社 | ペプチド化合物の環化方法 |
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2018
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- 2018-07-19 DK DK18785785.9T patent/DK3655395T3/da active
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- 2018-07-19 SI SI201830566T patent/SI3655395T1/sl unknown
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- 2018-07-19 AU AU2018304290A patent/AU2018304290B2/en not_active Ceased
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2020
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2022
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| ES2907640T3 (es) | 2022-04-25 |
| CN110933946A (zh) | 2020-03-27 |
| IL272034B (en) | 2022-06-01 |
| EP3655395A2 (en) | 2020-05-27 |
| PL3655395T3 (pl) | 2022-03-07 |
| US11254679B2 (en) | 2022-02-22 |
| AU2018304290A8 (en) | 2020-04-02 |
| US20200223852A1 (en) | 2020-07-16 |
| HUE058049T2 (hu) | 2022-06-28 |
| HRP20220264T8 (hr) | 2022-05-27 |
| WO2019018592A3 (en) | 2019-02-28 |
| US20220177482A1 (en) | 2022-06-09 |
| EP3655395B1 (en) | 2021-12-01 |
| IL272034A (en) | 2020-03-31 |
| WO2019018592A2 (en) | 2019-01-24 |
| KR20200031656A (ko) | 2020-03-24 |
| BR112020000418A2 (pt) | 2020-07-14 |
| SI3655395T1 (sl) | 2022-04-29 |
| EA202090346A1 (ru) | 2020-08-18 |
| CA3070423A1 (en) | 2019-01-24 |
| LT3655395T (lt) | 2022-03-10 |
| JP2020527576A (ja) | 2020-09-10 |
| RS62941B1 (sr) | 2022-03-31 |
| DK3655395T3 (da) | 2022-03-07 |
| PT3655395T (pt) | 2022-02-22 |
| CY1125023T1 (el) | 2023-03-24 |
| AU2018304290B2 (en) | 2022-11-17 |
| SG11202000441QA (en) | 2020-02-27 |
| IL293088A (en) | 2022-07-01 |
| AU2018304290A1 (en) | 2020-03-05 |
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