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nonce записывается в расширениях запроса https://datatracker.ietf.org/doc/html/rfc6960#page-35

TBSRequest      ::=     SEQUENCE {
    version             [0] EXPLICIT Version DEFAULT v1,
    requestorName       [1] EXPLICIT GeneralName OPTIONAL,
    requestList             SEQUENCE OF Request,
    requestExtensions   [2] EXPLICIT Extensions {{re-ocsp-nonce |
                     re-ocsp-response, ...,
                     re-ocsp-preferred-signature-algorithms}} OPTIONAL }

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import javax.security.auth.x500.X500Principal;
import kz.gov.pki.kalkan.asn1.ASN1Object;
import kz.gov.pki.kalkan.asn1.ASN1Sequence;
import kz.gov.pki.kalkan.asn1.ASN1Set;
import kz.gov.pki.kalkan.asn1.DERObjectIdentifier;
import kz.gov.pki.kalkan.asn1.DERString;
import kz.gov.pki.kalkan.asn1.x509.X509Name;
import kz.gov.pki.provider.utils.X509Util;

public class PlusSignSubjectDN {

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package kz.gov.pki.jwt;

import java.security.KeyPair;
import java.security.KeyPairGenerator;
import java.security.Provider;
import java.security.Security;
import java.security.interfaces.ECPrivateKey;
import java.security.interfaces.ECPublicKey;

import com.auth0.jwt.JWT;

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package kz.sample.jwt;

import java.io.ByteArrayInputStream;
import java.security.Signature;
import java.security.cert.CertificateFactory;
import java.security.cert.X509Certificate;
import java.util.Base64;
import org.apache.commons.lang3.StringUtils;
import lombok.extern.slf4j.Slf4j;

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package kz.gov.egg.sync.client;

import java.security.Security;
import java.util.HashMap;
import java.util.UUID;

import org.apache.cxf.ext.logging.LoggingFeature;
import org.apache.wss4j.common.crypto.WSProviderConfig;

import kz.gov.egg.sync.client.gbd.fl.UniFlSyncClient;

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package kz.gov.pki.sample;

import java.io.StringWriter;
import java.security.KeyStore;
import java.security.Provider;
import java.util.Enumeration;
import kz.gov.pki.kalkan.Storage;
import kz.gov.pki.kalkan.jce.provider.cms.CMSSignedData;
import kz.gov.pki.kalkan.openssl.PEMWriter;
import kz.gov.pki.provider.utils.CMSUtil;

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import java.io.ByteArrayInputStream;
import java.io.FileInputStream;
import java.io.IOException;
import java.io.StringWriter;
import java.security.KeyStore;
import java.security.PrivateKey;
import java.security.Provider;
import java.security.Security;
import java.security.cert.X509Certificate;
import java.util.Enumeration;

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package kz.gov.pki.samples;

import java.awt.Graphics;
import java.awt.Image;
import java.awt.Toolkit;
import java.awt.datatransfer.DataFlavor;
import java.awt.datatransfer.Transferable;
import java.awt.datatransfer.UnsupportedFlavorException;
import java.awt.image.BufferedImage;
import java.io.ByteArrayInputStream;

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BIO *not_before_bio = BIO_new(BIO_s_mem());
ASN1_TIME_print(not_before_bio, X509_get_notBefore(cert)); // format    MMM DD HH:MM:SS YYYY [GMT]
//    ASN1_STRING_print_ex(not_before_bio, X509_get_notAfter(cert), ASN1_STRFLGS_UTF8_CONVERT); // UTC format   YYMMDDHHMMSSZ
int not_before_len = BIO_number_written(not_before_bio);
unsigned char *not_before = (unsigned char *)calloc(not_before_len, sizeof(unsigned char));

BIO_read(not_before_bio, not_before, not_before_len);
NSLog(@"not before: %s", not_before);
BIO_free(not_before_bio);

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  BIO *in = NULL, *out = NULL;
  CMS_ContentInfo *cms = NULL;
  CMS_SignerInfo *si = NULL;
  unsigned char *cms_pem = NULL;
  int cms_flags = CMS_NOSMIMECAP | CMS_BINARY | CMS_PARTIAL | CMS_STREAM;
  int cms_pem_len = 0;

  NSString *nsstring = @"c2FtcGxl";
  const unsigned char *cstring = (const unsigned char *) [nsstring UTF8String];